CN104093308A - Pesticidal compositions and methods related thereto - Google Patents

Abstract

This document discloses molecules having the following formula (1) and processes related thereto.

Description

Pesticidal compositions and methods related thereto

Cross References to Related Applications

This application claims the benefit of and priority to US Provisional Application 61/551,575, filed October 26, 2011, which is hereby incorporated by reference in its entirety.

technical field

The present disclosure relates to methods of making molecules useful as insecticides, such as acaricides, insecticides, molluscicides and nematicides, said molecules and methods of using said molecules to control pests.

Background technique

Pests kill millions of people every year around the world. Additionally, there are more than 10,000 pest species that cause agricultural losses. Worldwide agricultural losses add up to billions of dollars each year.

Termites damage a variety of private and public structures. Worldwide termite damage costs total billions of dollars annually.

Pests in stored food eat and adulterate stored food. Worldwide losses of stored food add up to billions of dollars each year, but more importantly, deprive people of much-needed food.

New insecticides are urgently needed. Certain pests are developing resistance to currently used insecticides. Hundreds of pest species are resistant to one or more insecticides. The development of resistance to some older insecticides such as DDT, carbamates and organophosphates is well known. However, resistance has also developed to some newer insecticides.

Accordingly, new insecticides are needed for a number of reasons, including those described above.

Contents of the invention

definition

The examples given in the definitions are generally non-exhaustive and are not to be construed as limiting the invention disclosed in this application. It is understood that substituents should conform to the laws of chemical bonding and the constraints of stereochemical compatibility with respect to the particular molecule to which they are attached.

"Alkenyl" means an acyclic unsaturated (at least one carbon-carbon double bond) branched or unbranched substituent composed of carbon and hydrogen, such as vinyl, allyl, butenyl, pentyl, alkenyl and hexenyl.

"Alkenyloxy" means an alkenyl group further comprising a carbon-oxygen single bond, eg allyloxy, butenyloxy, pentenyloxy, hexenyloxy.

"Alkoxy" means an alkyl group that also contains a carbon-oxygen single bond, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, and tert-butoxy.

"Alkyl" means an acyclic saturated branched or unbranched substituent composed of carbon and hydrogen, such as methyl, ethyl, (C ₃ )alkyl (which means n-propyl and isopropyl ), (C ₄ )alkyl (which stands for n-butyl, sec-butyl, isobutyl, and tert-butyl).

"Alkynyl" means an acyclic unsaturated (at least one carbon-carbon triple bond) branched or unbranched substituent composed of carbon and hydrogen, such as ethynyl, propargyl, butynyl and pentynyl Alkynyl.

"Alkynyloxy" means an alkynyl group further comprising a carbon-oxygen single bond, eg, pentynyloxy, hexynyloxy, heptynyloxy and octynyloxy.

"Aryl" means a cyclic aromatic substituent composed of hydrogen and carbon, such as phenyl, naphthyl, and biphenyl.

"(C _x -C _y )" (where the subscripts "x" and "y" are integers, such as 1, 2, or 3) indicates the range of carbon atoms for a substituent – for example, (C ₁ -C ₄ )alkyl Each independently represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl.

"Cycloalkenyl" means a monocyclic or polycyclic unsaturated (at least one carbon-carbon double bond) substituent composed of carbon and hydrogen, such as cyclobutenyl, cyclopentenyl, cyclohexenyl, nor Bornyl, bicyclo[2.2.2]octenyl, tetrahydronaphthyl, hexahydronaphthyl and octahydronaphthyl.

"Cycloalkenyloxy" means a cycloalkenyl group further comprising a carbon-oxygen single bond, such as cyclobutenyloxy, cyclopentenyloxy, norbornenyloxy and bicyclo[2.2.2]octyloxy Alkenyloxy.

"Cycloalkyl" means a monocyclic or polycyclic saturated substituent composed of carbon and hydrogen, such as cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, bicyclo[2.2.2]octyl and Decalinyl.

"Cycloalkoxy" means a cycloalkyl group also containing a carbon-oxygen single bond, such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, norbornyloxy and bicyclo[2.2.2 ] Octyloxy.

"Halogen" means fluorine, chlorine, bromine and iodine.

"Haloalkoxy" means an alkoxy group further comprising from one to the maximum possible number of identical or different halogens, for example fluoromethoxy, trifluoromethoxy, 2,2-difluoropropoxy, chloromethoxy , trichloromethoxy, 1,1,2,2-tetrafluoroethoxy, and pentafluoroethoxy.

"Haloalkyl" means an alkyl group further comprising from one to the maximum possible number of identical or different halogens, for example fluoromethyl, trifluoromethyl, 2,2-difluoropropyl, chloromethyl, trichloromethyl and 1,1,2,2-Tetrafluoroethyl.

"Heterocyclyl" means a cyclic substituent, which may be fully saturated, partially unsaturated, or fully unsaturated, wherein the ring structure contains at least one carbon and at least one heteroatom, wherein the heteroatom is nitrogen, sulfur or oxygen. In the case of sulfur, this atom can be in other oxidation states such as sulfoxide and sulfone. Examples of aromatic heterocyclic groups include, but are not limited to, benzofuryl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, benzothienyl, benzothiazolyl, cinnolinyl, furanyl base, imidazolyl, indazolyl, indolyl, isoindolyl, isoquinolyl, isothiazolyl, isoxazolyl, oxadiazolyl, oxazolinyl, oxazolyl, phthalazinyl, Pyrazinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl, quinoxalinyl, tetrazolyl, thiazolinyl, thiazolyl , thienyl, triazinyl, and triazolyl. Examples of fully saturated heterocyclic groups include, but are not limited to, piperazinyl, piperidinyl, morpholinyl, pyrrolidinyl, oxetanyl, tetrahydrofuranyl, tetrahydrothiophenyl, and tetrahydropyranyl. Examples of partially unsaturated heterocyclic groups include, but are not limited to, 1,2,3,4-tetrahydroquinolyl, 4,5-dihydro-oxazolyl, 4,5-dihydro-1H-pyrazolyl, 4,5-dihydro-isoxazolyl, and 2,3-dihydro-[1,3,4]-oxadiazolyl. Additional examples include the following

Detailed ways

The present application discloses molecules having the following formula ("Formula 1"):

in

(a) X is N or CR8;

(b) R1 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, C(=X1)R9, C(= X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n OR9, or R9S(O) _n R9,

Wherein each of the substituted R1 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9);

(c) R2 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, C(=X1)R9, C(= X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n OR9, or R9S(O) _n R9,

Wherein each of the substituted R2 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9);

(d) R3 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, C(=X1)R9, C(= X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n OR9, or R9S(O) _n R9,

Wherein each of the substituted R3 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9);

(e) R4 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, C(=X1)R9, C(= X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n OR9, or R9S(O) _n R9,

Wherein each of the substituted R4 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9);

(f) R5 is R11, H, substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N( R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n OR9, R9S(O) _n R9, C ₁ -C ₆ alkyl C ₆ -C ₂₀ aryl (wherein the alkyl and aryl groups can be independently substituted or unsubstituted), C(=X2)R9, C(=X1)X2R9, R9X2C(=X1)R9, R9X2R9, C(=O) (C ₁ -C ₆ alkyl)S(O) _n (C ₁ -C ₆ alkyl), C(=O)(C ₁ -C ₆ alkyl)C(=O)O(C ₁ -C ₆ Alkyl), (C ₁ -C ₆ alkyl)OC(=O)(C ₆ -C ₂₀ aryl), (C ₁ -C ₆ alkyl)OC(=O)(C ₁ -C ₆ alkyl ), C ₁ -C ₆ alkyl-(C ₃ -C ₁₀ ring haloalkyl), or (C ₁ -C ₆ alkenyl) C (=O) O (C ₁ -C ₆ alkyl), or R9X2C ( =X1)X2R9;

Wherein each of the substituted R5 (except R11) has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ - C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ Cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl Base, or C ₁ -C ₂₀ heterocyclyl, R9 aryl (wherein each substitutable substituent may be optionally substituted with R9)

Optionally, R5 (except R11) and R7 may be connected in a ring arrangement, wherein optionally, such arrangement may have one or more selected from O, S or N heteroatoms;

(g) R6 is O, S, NR9, or NOR9;

(h) R7 is substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, OR9S(O) _n R9, C(=X1)R9, C(=X1)OR9, R9C(=X1 )OR9, R9X2C(=X1)R9X2R9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)(R9S(O)nR9), _N (R9)C(=X1)R9 , SR9, S(O) _n OR9, R9S(O) _n R9, C ₁ -C ₆ alkyl OC(=O)C ₁ -C ₆ alkyl, OC ₁ -C ₆ alkyl C ₁ -C ₂₀ hetero Cyclic group, C ₁ -C ₆ alkyl C ₁ -C ₂₀ heterocyclyl, C ₁ -C ₆ alkyl S(=N-CN)(C ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl S(O)(=N-CN)(C ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl S(O) _n (C ₁ -C ₆ alkyl, C ₁ -C ₂₀ heterocyclyl), C ₁ -C ₆ alkyl S(O)(=N-CN)(C ₁ -C ₆ alkyl-C ₁ -C ₂₀ heterocyclyl), C ₁ -C ₆ alkyl NH(C(=O) OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl C(=O)OC ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl (C ₆ -C ₂₀ aryl) NH(C(= O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl (SC ₁ -C ₆ alkyl) NH (C(=O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl (SC ₁ -C ₆ alkyl-C ₆ -C ₂₀ aryl)NH(C(=O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl (NHC(=O)OC ₁ -C ₆ alkyl C ₆ -C ₂₀ aryl) NH(C(=O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl (OC ₁ -C ₆ alkyl C ₆ -C ₂₀ aryl) NH(C(=O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl N(C ₁ -C ₆ alkyl)(C(=O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl NH (C ₁ -C ₆ alkyl), C ₆ -C ₂₀ arylSC ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkyl-N (C ₁ -C ₆ alkyl) ( C(=O)C ₁ -C ₆ alkyl (C ₆ -C ₂₀ aryl), C ₁ -C ₆ alkyl N (C ₁ -C ₆ alkyl) (C ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl N (C ₁ -C ₆ alkyl)(S(O) _n C ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl N(C ₁ -C ₆ alkyl) (S(O) _n C ₁ -C ₆ alkene C ₆ -C ₂₀ aryl), C ₁ -C ₆ alkyl N(C ₁ -C ₆ alkyl) (C(=O)C ₁ -C ₂₀ heterocyclyl), C ₁ -C ₆ alkyl N(C ₁ -C ₆ alkyl)(C(=O)OC ₁ -C ₆ alkylC ₆ -C ₂₀ aryl), NH(C ₁ -C ₆ alkylS(O) _n C ₁ -C ₆ alkyl), NH (C ₁ -C ₆ alkyl S(O) _n C ₆ -C ₂₀ aryl), C ₁ -C ₆ alkyl (S(O) _n C ₁ -C ₆ alkyl) ( C(=O)C ₁ -C ₆ alkylS(O) _n (C ₁ -C ₆ alkyl), or R9S(O) _n (NZ)R9,

Wherein each of the substituted R7 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9), C(=X1)R9, C(=X1)OR9, C(=X1)N(R9) ₂ , =X2, N(R9) ₂ , S(=X2) _n R9, R9S(O) _n R9, S(O) _n N(R9) ₂ ;

(i) R8 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, C(=X1)R9, C(= X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n R9, S(O) _n OR9, or R9S (O) _n R9,

Wherein each of the substituted R8 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9);

(j) R9 (each independently) is H, CN, substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ ring Alkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, S(O) _n C ₁ -C ₆ alkyl, N(C ₁ - C ₆ alkyl) ₂ ,

Wherein each of the substituted R9 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OC ₁ -C ₆ alkyl, OC ₁ -C ₆ haloalkyl, S(O) _n C ₁ -C ₆ alkyl, S(O) _n OC ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, or C ₁ -C ₂₀ heterocyclic;

(k) R10 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n OR9, or R9S(O) _n R9,

Wherein each of the substituted R10 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, or C ₆ -C ₂₀ aryl (wherein each Substitutable substituents may optionally be substituted with R9);

(l) n is (each independently) 0, 1, or 2;

(m) X1 is (each independently) O or S;

(n) X2 is (each independently) O, S, =NR9, or =NOR9;

(o) R11 is Q ₁ (C≡C)R12, wherein Q ₁ is a bond, substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₂ -C ₆ alkynyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₂ -C ₁₀ cycloalkoxy, substituted or unsubstituted C ₁ -C ₆ alkyl OR9, substituted or unsubstituted C ₁ -C ₆ alkyl S(O) _n R9, substituted or unsubstituted C ₁ -C ₆ alkyl S(O) _n (=NR9) , substituted or unsubstituted C ₁ -C ₆ alkyl N(R9) (wherein (C≡C) is directly connected to N via a bond), substituted or unsubstituted C ₁ -C ₆ alkyl N(R9) _2. Substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₀ -C ₆ alkyl C(=R6 )C ₀ -C ₆ alkyl R9, substituted or unsubstituted C ₀ -C ₆ alkyl C(=R6)OR9, substituted or unsubstituted C ₁ -C ₆ alkylOC ₀ -C ₆ alkyl C(=R6)R9, substituted or unsubstituted C ₁ -C ₆ alkyl N(R9)(C(=R6)R9), substituted or unsubstituted C ₁ -C ₆ alkyl N(R9) (C(=R6)OR9), substituted or unsubstituted C ₀ -C ₆ alkyl C(=R6)C ₀ -C ₆ alkyl N(R9) (where (C≡C) is directly bonded to N through a bond Link), substituted or unsubstituted C ₀ -C ₆ alkyl C(=R6)C ₀ -C ₆ alkyl N(R9) ₂ , OR9, S(O) _n R9, N(R9)R9, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl,

Wherein each of the substituted Q ₁ has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, SR9, S(O) _n R9, S (O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ -C ₂₀ heterocyclyl, R9 aryl, C ₁ -C ₆ alkyl OR9, C ₁ -C ₆ alkyl S(O) _n R9 (wherein each substitutable substituent may optionally be substituted with R9)

Optionally, _Q1 and R7 can be connected in a ring arrangement, wherein optionally, this arrangement can have one or more heterogeneous compounds selected from O, S, or N in the ring structure connecting _Q1 and R7. atom;

(p) R12 is _Q1 (except for the case where _Q1 is a bond), F, Cl, Br, I, Si(R9) ₃ (wherein each R9 is independently selected), or R9; and

(q) Z is CN, NO ₂ , C ₁ -C ₆ alkyl (R9), C(=X1)N(R9) ₂ .

Formula 1 and its subparts (a) to (o) are hereinafter referred to as "Embodiment A1".

In another embodiment of this molecule, X is CR8.

In another embodiment of this molecule, R1 is H.

In another embodiment of this molecule, R2 is H.

In another embodiment of this molecule, R3 is H.

In another embodiment of this molecule, R4 is halo or unsubstituted _C1 - _C6 alkyl.

In another embodiment of this molecule, R4 is F, Cl, or unsubstituted _C1 - _C2 alkyl.

In another embodiment of this molecule, R4 is Cl, or _CH3 .

In another embodiment of this molecule, R5 is H, substituted or unsubstituted _C1 - _C6 alkyl.

In another embodiment of this molecule R5 is substituted _C1 - _C6 alkyl substituted with _C3 - _C10 cycloalkyl.

In another embodiment _of this molecule, R5 is H, _CH3 , _CH2 -cyclopropyl, or _CH2CH3 .

In another embodiment of this molecule, R6 is O.

In another embodiment of this molecule, R7 is a substituted or unsubstituted _C1 - _C6 alkyl, OR9, or R9S(O) _nR9 .

In another embodiment of this molecule R7 is a substituted Ci _{- C6} alkyl wherein said substituents are one or more halogens.

In another embodiment of this molecule, R7 is a substituted _C1 - _C6 alkyl, wherein said substituents are one or more F or Cl or combinations thereof.

In another embodiment of this molecule R7 is a substituted _C1 - _C6 alkyl wherein said substituents are one or more F.

In another embodiment _of this molecule R7 is _CH2CF3 .

In another embodiment of this molecule, R7 is unsubstituted _C1 - _C6 alkyl.

In another embodiment _of this _molecule , R7 is CH( _CH3 ) ₂ , _CH3 , C( _CH3 ) ₃ , or _{CH2CH2CH2CH3 .}

In another embodiment of this molecule, R7 is OR9.

In another embodiment of this molecule, R7 is O(unsubstituted _C1 - _C6 alkyl).

In another embodiment of this molecule R7 is OC( _CH3 ) ₃ .

In another embodiment of this molecule R7 is R9S(O) _nR9 .

In another embodiment of this molecule R7 is (unsubstituted C ₁ -C ₆ alkyl)S(unsubstituted C ₁ -C ₆ alkyl).

In another embodiment of this molecule, R7 is _{CH2CH ( CH3} ) _SCH3 , _{CH2CH2SCH3 ,} CH( _CH3 ) _{2SCH3 ,} or CH( _CH3 ) _{CH2SCH3 .}

In another embodiment of this molecule R8 is H or halo.

In another embodiment of this molecule, R8 is H, F, or Cl.

In another embodiment of this molecule R8 is H or F.

In another embodiment of this molecule, R9 is unsubstituted _C1 - _C6 alkyl.

In another embodiment of this molecule, R10 is H or unsubstituted _C1 - _C6 alkyl.

In another embodiment of this molecule R10 is H or _CH3 .

In another embodiment of this molecule, n is zero.

In another embodiment of the present invention, R11 is substituted or unsubstituted C ₁ -C ₆ alkyl C≡CR12.

In another embodiment of the invention R11 is _CH2C≡CH .

Molecules of Formula 1 will generally have a molecular weight of from about 100 Daltons to about 1200 Daltons. However, molecular weights from about 120 Daltons to about 900 Daltons are generally preferred, and molecular weights from about 140 Daltons to about 600 Daltons are generally even more preferred.

The following scheme illustrates the route to 2-methylimidazolamide. In step a of Scheme I, a compound of formula III is treated with ethyl iminoacetate hydrochloride of formula IV, wherein R5 is as defined in embodiment A1 and R4 is methyl, to give the corresponding acetamidine of formula V. In step b of Scheme I, the α-bromoketone of formula II (wherein R1, R2, R3, R10, and X are as defined in Embodiment A1) can be obtained in the presence of an organic base such as triethylamine in polar properties Treatment with acetamidine of formula V in a subsolvent such as ethanol affords N-Boc-aminoimidazole of formula Ia. When R5=H, the carbamate of formula Ia (wherein R1, R2, R3, R4, R10 and X are as defined in embodiment A1) can be obtained in the presence of a base such as sodium hydride and an alkyl halide such as methyl iodide , alkylation in a protic polar solvent such as N,N-dimethylformamide affords compounds of formula Ib, as shown in step e of Scheme I. Deprotection of tert-butyl carbamates of formula Ia can be carried out as shown in step c of scheme I with trifluoroacetic acid (TFA) in a polar aprotic solvent such as dichloromethane (DCM) to give amino groups of formula Via Imidazole, wherein R1, R2, R3, R4, R10, R5 and X are as defined in Embodiment A1. In step d of Scheme I, the compound of formula VIa can be prepared in the presence of an organic base such as N,N-dimethylaminopyridine (DMAP) and an inorganic base such as potassium carbonate in a polar aprotic solvent such as 1,2- Treatment with an acid chloride of formula VII wherein R7 is as defined in Embodiment A1 in ethyl chloride (DCE) affords compounds of formula Ic.

Option I

Another route to imidazolamides is described in Scheme II. Diketones of formula VIII, wherein R1, R2, R3, R10 and X are as defined in embodiment A1, can be prepared in a protic solvent such as methanol with an aldehyde such as acetaldehyde, an ammonia source such as ammonium acetate and a catalyst such as indium chloride ( III) treatment to obtain the compound of formula IX. A compound of formula IX, wherein R1, R2, R3, R4, R10 and X are as defined in embodiment A1, can be treated with a base such as sodium hydride in a solvent such as THF and added an oxaziridine of formula Xa to give A compound of formula Id, wherein R5 is H.

Scheme II

Another route to imidazolamides is described in Scheme III. Substituted 2-aminoimidazoles of formula XI were prepared according to the general procedure described in J. Med. Chem., 2010, 53, 2409 by Li and co-workers. Compounds of formula XI, wherein R1, R2, R3, R10, and X are as defined in Embodiment Al, are treated under Sandmeyer conditions to form compounds of formula XII, wherein R4 is halogen, as shown in step a of Scheme III. Hydrazones of formula XII can be converted to the corresponding amines of formula VIb (where R5 is H) when treated with hydrazine in a polar protic solvent such as 2-methoxyethanol, as shown in step b.

Scheme III

Another route to imidazolamides is described in Scheme IV. Imidazoles of formula XIII (where R and R are as defined in embodiment A1 and Q is halogen (e.g., bromine)) can be dissolved in a polar aprotic solvent such as tetrahydrofuran and an aminating reagent such as an oxaziridine of formula Xb, Treatment with a base such as sodium hydride affords compounds of formula XIVa as shown in step a of Scheme IV. Carbamates of formula XIVa can be alkylated in polar aprotic solvents such as N,N-dimethylformamide in the presence of a base such as sodium hydride and an alkyl halide such as ethyl iodide to give formula XIVb Compounds wherein R5 is alkyl, as shown in step b. Compounds of formula XIVb (wherein R4, R5 and R10 are as defined in embodiment A1) can be reacted under Suzuki coupling conditions with boronic acids of formula XV (wherein X, R1, R2 and R3 are as defined in embodiment A1) to provide formula Heterocycle-coupled imidazoles of Ie, as in step c. When R4 = H, compounds of formula Ie can be halogenated in the presence of a base such as n-butyllithium in a polar aprotic solvent such as tetrahydrofuran and a hydrophilic source of halogen such as hexachloroethane to give 2-halogenated compounds of formula If Imidazole, wherein R4 is halogen and R1, R2, R3, R5, R10 and X are as defined in embodiment A1, as shown in step d.

Plan IV

In step a of Scheme V, a compound of formula Ig (wherein R7 is tert-butoxy) is treated with a reagent such as propargyl bromide in the presence of a base such as sodium hydride and in a polar aprotic solvent such as DMF to provide formula Ih Compounds wherein R5=R11.

Plan V

Example

The examples are for illustrative purposes and should not be construed to limit the invention disclosed in this application to only the embodiments disclosed in these examples.

Commercially available starting materials, reagents and solvents were used without further purification. Anhydrous solvents were purchased from Aldrich as Sure/Seal ^™ and used as received. Melting points were obtained by Thomas Hoover Unimelt capillary melting point apparatus or OptiMelt Automated MeltingPoint System from Stanford Research Systems and are uncorrected. Molecules are given by their known names according to the naming program in ISIS Draw, ChemDraw or ACD Name Pro. If the program is unable to name a molecule, the molecule is named using conventional naming conventions. All NMRs are given in ppm ([delta]) and were recorded at 300, 400 or 600 MHz unless otherwise stated.

Example 1, Step 1: Preparation of N'-(1-imino-ethyl)-N-methyl-hydrazine carboxylic acid tert-butyl ester

tert-butyl 1-methylhydrazinecarboxylate (10.0g, 68.4mmol), ethyl iminoacetate hydrochloride (42.1g, 342mmol), and potassium carbonate (K ₂ CO ₃ ; 94.4g, 684mmol ) in N,N-dimethylformamide (DMF; 150 mL) was heated at 105° C. for 5 hours (h). The contents were cooled to 0 °C, then the precipitated material was collected by vacuum filtration and resuspended in _H2O (100 mL). After 30 minutes (min) of vigorous stirring, the remaining precipitate was collected and dried in a vacuum oven at 45 °C overnight to afford the title compound as a white solid (7.56 g, 59.0%): mp 187-189 °C; ¹ H NMR (400MHz,DMSO-d ₆ )δ6.28(br s,1H),2.77(s,3H),1.64(s,3H),1.36(s,9H).

Example 1, Step 2: Preparation of methyl-(2-methyl-4-pyridin-3-yl-imidazol-1-yl)-carbamic acid tert-butyl ester (compound 3)

N'-(1-imino-ethyl)-N-methyl-hydrazinecarboxylate tert-butyl ester (5.00g, 26.7mmol) and triethylamine (TEA; 9.30mL, 66.8mmol) in ethanol (EtOH ; 100 mL) was added portionwise with 2-bromo-1-pyridin-3-yl-ethanone hydrobromide (8.99 g, 32.0 mmol). The contents were heated at 80 °C for 3 hours, then the solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography (dichloromethane (DCM):methanol (MeOH), 10:1 ) to afford the title compound as orange Oil (1.55g, 20.1%): ¹ H NMR (400MHz, CDCl ₃ ) δ8.92(d, J=2.4Hz, 1H), 8.43(dd, J=4.9, 1.4Hz, 1H), 8.03(dt ,J=8.3,1.6Hz,1H),7.28(dd,J=7.7,4.8Hz,1H),7.21(s,1H),3.38(s,3H),2.36(s,3H),1.43(s, 9H); ESIMS m/z289([M+H] ⁺ ).

Example 1, Step 3: Preparation of methyl-(2-methyl-4-pyridin-3-yl-imidazol-1-yl)-amine

Method A:

Methyl-(2-methyl-4-pyridin-3-yl-imidazol-1-yl)carbamate tert-butyl ester (1.50 g, 5.20 mmol) and trifluoroacetic acid (0.40 mL, 5.20 mmol) were dissolved in DCM (5 mL) was stirred at ambient conditions for 3 hours. The solvent was removed under reduced pressure and the residue was resuspended in DCM (10 mL) followed by the addition of TEA (1.45 mL, 10.4 mmol). After stirring for 10 minutes, the solvent was removed and the residue was purified by silica gel chromatography (DCM:MeOH, 10:1) to give an inseparable mixture of the title compound and triethylammonium salt (822mg). The mixture was used in subsequent reactions without further purification.

Method B:

A solution of tert-butyl methyl(2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-yl)carbamate (2.7 g, 9.4 mmol) in DCM (50 mL) was washed with hydrogen chloride (HCl)/dioxane (4 molar (M), 20 mL) treatment. The mixture was stirred overnight at room temperature. Filtration of the precipitate gave the title compound as a brown solid (1.15 g, 54.5%): ¹ H NMR (300 MHz, DMSO-d ₆ ) δ 9.41-9.32 (m, 1H), 8.82-8.56 (m, 3H), 7.97-7.89(m,1H),2.85(s,3H),2.67(d,J＝3.0Hz,3H); ESIMSm/z189([M+H] ⁺ ).

2-Methyl-N-(prop-2-yn-1-yl)-4-(pyridin-3-yl)-1H-imidazol-1-amine As disclosed in Example 1, Step 3, Method A Preparation by operation: ¹ H NMR (300MHz, CDCl ₃ ) δ8.90(s, 1H), 8.41(d, J=3.9Hz, 1H), 8.02(dt, J=7.9, 1.8Hz, 1H), 7.49(s ,1H),7.26(dd,J=7.9,4.8Hz,1H),5.86(t,J=5.2Hz,1H),3.84(dd,J=5.2,2.4Hz,2H),2.44(s,3H) , 2.41 (t, J=2.4Hz, 1H); ¹³ C NMR (75MHz, CDCl ₃ ) δ147.51, 146.48, 146.28, 134.99, 131.88, 130.41, 123.48, 115.28, 79.47, 74.21, 42.18, 12.28; ESIMS m/z 213 ([M+H] ⁺ ).

N-Ethyl-2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-amine was prepared according to the procedure disclosed in Example 1, Step 3, Method B: ¹ H NMR (300 MHz, DMSO-d ₆ )δ9.32(s,1H),8.76-8.69(m,2H),8.57-8.46(m,1H),7.81(s,1H),3.12-3.03(m,2H),2.63( s,3H),1.06(t,3H,J＝7.2Hz); ESIMS m/z203([M+H] ⁺ ).

N-(cyclopropylmethyl)-2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-amine was prepared according to the procedure disclosed in Example 1, Step 3, Method B: ¹ H NMR (300MHz,DMSO-d ₆ )δ9.26(s,1H),8.74-8.72(m,1H),8.67-8.59(m,1H),8.51-8.46(m,1H),7.81(s, 1H),2.95(d,2H,J=7.2Hz),2.66(s,3H),0.93-0.86(m,1H),0.46-0.43(m,2H),0.07-0.06(m,2H); m/z229([M+H] ⁺ ).

4-(5-fluoropyridin-3-yl)-N,2-dimethyl-1H-imidazol-1-amine was prepared according to the procedure disclosed in Example 1, Step 3, Method B: ¹ H NMR (300 MHz ,CD ₃ OD)δ9.05(s,1H),8.84(s,1H),8.47-8.44(m,2H),2.97(s,3H),2.74(s,3H); ESIMSm/z207([M +H] ⁺ ).

N-Ethyl-4-(5-fluoropyridin-3-yl)-2-methyl-1H-imidazol-1-amine was prepared according to the procedure disclosed in Example 1, Step 3, Method B: ¹ H NMR (300MHz,CD ₃ OD)δ8.99(s,1H),8.80(s,1H),8.41-8.35(m,2H),3.26(q,J＝7.2Hz,2H),2.74(s,3H) ,1.19(t,3H,J＝7.2Hz); ESIMSm/z221([M+H] ⁺ ).

N-(Cyclopropylmethyl)-4-(5-fluoropyridin-3-yl)-2-methyl-1H-imidazol-1-amine According to the procedure disclosed in Example 1, Step 3, Method B Preparation: ¹ H NMR (300MHz, CD ₃ OD) δ8.965(s,1H),8.746(s,1H),8.39-8.30(m,2H),3.08-3.05(m,2H),2.77(s, 3H),1.08-0.95(m,1H),0.56-0.56(m,2H),0.19-0.15(m,2H); ESIMSm/z247([M+H] ⁺ ).

Example 1, Step 4: Preparation of N-methyl-N-(2-methyl-4-pyridin-3-yl-imidazol-1-yl)-3-methylsulfanylbutanamide (compound 2)

Methyl-(2-methyl-4-pyridin-3-yl-imidazol-1-yl)-amine (400mg, 2.13mmol), 3-methylsulfanyl butanoyl chloride (649mg, 4.25mmol), 4 - A solution of dimethylaminopyridine (DMAP; (260 mg, 2.13 mmol), and K ₂ CO ₃ (881 mg, 6.38 mmol) in 1,2-dichloroethane (DCE; 5 mL) was heated at 80° C. for 6 hours The solvent was removed under reduced pressure and the residue was purified by reverse phase chromatography (0-100% acetonitrile/water) to afford the title compound as a brown oil (290 mg, 44.8%): ¹ H NMR (400 MHz, CDCl ₃ ) δ8.94(brs,1H),8.47(dd,J＝5.0,1.4Hz,1H),8.04(dt,J＝8.2,1.5Hz,1H),7.36-7.27(m,2H),3.39(s, 3H), 3.25-3.18(m,1H), 2.38(s,3H), 2.27-2.19(m,2H), 2.02(s,3H), 1.24(d,J=6.2Hz,3H); ESIMS m/ z304([M+H] ⁺ ).

Compounds 1 and 5-38 were prepared according to the procedure disclosed in Example 1.

Example 2, Step 1: Preparation of 3-(2,5-Dimethyl-1H-imidazol-4-yl)pyridine

Compounds were prepared following the general procedures disclosed in: Sharma, SD; Hazarika, P.; Konwar, D. Tetrahedron Lett. 2008, 49, 2216. 1-pyridin-3-yl-propane-1,2-dione (such as Knaus, EE; Avasthi, K.; Redda, K.; Benderly, A.Can.J.Chem.1980,58(2), Prepared by the procedure described in 130; 0.50 g, 3.35 mmol), ammonium acetate ( _NH4OAc ; 0.517 g, 6.71 mmol) and indium(III) chloride (0.074 g, 0.033 mmol) were weighed into a 50 mL round bottom flask . Methanol (MeOH; 7 mL) and acetaldehyde (0.148 g, 0.190 mL, 3.35 mmol) were added via syringe, and the cloudy mixture was stirred vigorously overnight. Thin layer chromatography analysis (TLC; CH ₂ Cl ₂ (DCM):MeOH/10:1 indicated that some starting material remained. Additional ammonium acetate (0.517 g, 6.71 mmol), indium(III) chloride (0.074 g, 0.033mmol) and acetaldehyde (0.148g, 0.190mL, 3.35mmol), and stirred again overnight. The mixture was filtered through filter paper, washed with MeOH to remove the precipitate, and then concentrated to low volume. The residue was subjected to flash silica gel chromatography (DCM:MeOH/10:1) to give the low R _f compound. The material was dissolved in a minimum amount of DCM and treated with saturated aqueous sodium bicarbonate (NaHCO ₃ ). The resulting precipitate was collected by filtration and washed with water and DCM, and dried to give 0.105 g of a pale yellow powder. The layers of the filtrate were _separated , and the aqueous phase was repeatedly extracted with DCM and ethyl acetate (EtOAc). The combined extracts were dried over _Na2SO4 , filtered and concentrated , to give an additional 0.06 g of the title compound as a yellow-orange solid (0.165 g, 28%): mp 179–181° C.; ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.85 (bs, 1H), 8.46 (d, J= 4.1Hz, 1H), 7.99(bs, 1H), 7.31(dd, J=7.7, 4.7Hz, 1H), 2.44(s, 6H); ESIMS m/z174([M+H] ⁺ ). and 172( [MH] ^- ).

Example 2, Step 2: Preparation of tert-butyl (2,5-dimethyl-4-pyridin-3-yl-imidazol-1-yl)carbamate (Compound 4)

3-(2,5-Dimethyl-1H-imidazol-4-yl)pyridine (0.035 g, 0.220 mmol) was weighed into an oven-dried, nitrogen-purged 10 mL round bottom flask. Tetrahydrofuran (THF, 1 mL) was added via syringe and the resulting slurry was cooled with stirring on an ice bath under nitrogen and treated with sodium hydride (0.0097 g, 0.242 mmol. 60% dispersion in oil). After 10 minutes, tert-butyl 3-(4-cyano-phenyl)oxaziridine-2-carboxylate (0.052 g, 0.212 mmol) was added as a solid and the thick yellow slurry was allowed to warm to room temperature and stirred for 2 hours. The crude reaction mixture was loaded directly onto a flash silica gel column and eluted with DCM:MeOH (10:1) to afford (2,5-Dimethyl-4-pyridin-3-yl-imidazol-1 -yl) tert-butyl carbamate as a 5:1 mixture with its regioisomer (0.027 g, 46%): IR (thin layer) 3389, 2978, 2930, 1730, 1478, 1275, 1252, 1156,1017,951,711,573cm ^-1 ; ¹ H NMR (300MHz, DMSO, main isomer) δ10.41(s,1H),8.81(s,1H),8.39(s,1H),7.95(d,J ＝8.0Hz,1H),7.44–7.28(m,1H),2.21(s,3H),2.18(s,3H),1.46(s,9H); ESIMS m/z289([M+H] ⁺ ). and 287([MH] ^- ).

Example 3: Preparation of (2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-yl)-tert-butyl carbamate

To a mixture of ethyl iminoacetate hydrochloride (2.0 g, 16.20 mmol) and TEA (3.28 g, 32.4 mmol) in EtOH (40 mL) was added tert-butyl hydrazinecarboxylate (2.14 g, 16.20 mmol) at room temperature. mmol) in EtOH (10 mL). The resulting mixture was stirred overnight at room temperature. To the resulting mixture was added a solution of 2-bromo-1-(pyridin-3-yl)ethanone hydrobromide (5.0 g, 17.9 mmol) and TEA (4.9 g, 48.6 mmol) in EtOH (20 mL). The reaction mixture was stirred at room temperature for 5 hours, then heated to reflux and stirred overnight. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (DCM:MeOH, 10:1) to afford the title compound as an orange oil (0.76 g, 17.3%): ¹ HNMR (300 MHz, CDCl ₃ ) δ8. 87(s,1H),8.45(d,1H,J=6.3Hz),8.43(s,1H),8.05(d,1H,J=6.3Hz),7.33-7.25(m,2H),2.37(s ,3H),1.51(s,9H); ESIMS m/z275([M+H] ⁺ ).

Example 4: Preparation of tert-butyl methyl(2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-yl)carbamate (Compound 3) (another method for preparing Compound 3 )

To a solution of tert-butyl 2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-ylcarbamate (2.0 g, 7.3 mmol) in dry DMF (15 mL) at 0 °C Sodium hydride (NaH; 0.35 g, 8.7 mmol, 60% dispersion in oil) was added. The reaction mixture was stirred at 0 °C for 30 minutes, then methyl iodide (1.55 g, 10.9 mmol) was added portionwise. The reaction mixture was stirred at 0 °C for 3 hours, then allowed to warm to ambient temperature. The reaction mixture was extracted with EtOAc (15 mL x2). The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate (Na ₂ SO ₄ ), filtered and concentrated to give the title compound (1.18 g, 56.2%) as an orange oil without further purification Just used in the next step: ¹ H NMR (300MHz, CDCl ₃ ): δ8.96(s,1H),8.49(s,1H),8.16-8.13(m,1H),7.38-7.36(m,2H), 3.36(s,3H),2.35(s,3H),1.44(s,9H); ESIMS m/z289([M+H] ⁺ ).

tert-butyl ethyl(2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-yl)carbamate was prepared according to the procedure disclosed in Example 4: ¹ H NMR (300 MHz, CDCl ₃ )δ8.94(s,1H),8.48-8.46(m,1H),8.09-8.05(m,1H),7.31-7.29(m,1H),7.20(s,1H),3.86-3.67(m, 2H),2.34(s,3H),1.44(s,9H),1.21(t,J=7.2Hz,3H); ESIMS m/z303([M+H] ⁺ ).

(Cyclopropylmethyl)(2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-yl)carbamate tert-butyl ester Prepared according to the procedure disclosed in Example 4: ¹ H NMR (300MHz, CDCl ₃ )δ8.94(s,1H),8.48-8.46(m,1H),8.10-8.06(m,1H),7.31-7.28(m,1H),7.25(s,1H),3.59 -3.54(m,2H),2.37(s,3H),1.44(s,9H),1.05-0.93(m,1H),0.56-0.53(m,2H),0.20-0.15(m,2H); ESIMS m/z329([M+H] ⁺ ).

tert-butyl (4-(5-fluoropyridin-3-yl)-2-methyl-1H-imidazol-1-yl)(methyl)carbamate was prepared according to the procedure disclosed in Example 4: ¹ H NMR (300MHz, CDCl ₃ )δ8.72(s,1H),8.31(d,J＝2.7Hz,1H),7.83-7.78(m,1H),7.27(s,1H),3.36(s,3H), 2.34(s,3H),1.44(s,9H); ESIMS m/z307([M+H] ⁺ ).

tert-butyl ethyl(4-(5-fluoropyridin-3-yl)-2-methyl-1H-imidazol-1-yl)carbamate was prepared according to the procedure disclosed in Example 4: ¹ H NMR (300 MHz ,CDCl ₃ )δ8.73(s,1H),8.32-8.31(m,1H),7.84-7.80(m,1H),7.23(s,1H),3.87-3.70(m,2H),2.34(s ,3H),1.45(s,9H),1.21(t,J＝7.2Hz,3H); ESIMS m/z321([M+H] ⁺ ).

(Cyclopropylmethyl)(4-(5-fluoropyridin-3-yl)-2-methyl-1H-imidazol-1-yl)carbamate tert-butyl ester was prepared according to the procedure disclosed in Example 4: ¹ H NMR (300MHz, CDCl ₃ )δ8.7s(s,1H),8.30-8.29(m,1H),7.85-7.80(m,1H),7.27(s,1H),3.57-3.54(m,2H ),2.37(s,3H),1.44(s,9H),1.02-0.93(m,1H),0.55-0.53(m,2H),0.21-0.17(m,2H); ESIMS m/z347([M +H] ⁺ ).

Example 5, Step 1: Preparation of E-2-chloro-N-(4-chlorobenzylidene)-4-(pyridin-3-yl)-1H-imidazol-1-amine

To (E)-N ¹ -(4-chlorobenzylidene)-4-(pyridin-3-yl)-1H-imidazole-1,2-diamine (5.3g, 18mmol) and CuCl (1.79 g, 18 mmol) in acetonitrile (100 mL) was added isoamyl nitrite (3.15 g, 27 mmol). The reaction mixture was stirred at room temperature for 1 hour, then heated to 70 °C for 3 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (petroleum ether:EtOAc, 2:1) to give the title compound (258 mg, 4%) as a white solid: ¹ H NMR (300 MHz, CDCl ₃ ) δ8.99(s,1H),8.55-8.54(m,1H),8.42(s,1H),8.17-8.13(m,1H),7.86-7.83(m,3H),7.50(d,J＝8.4 Hz,2H),7.36-7.31(m,1H); ESIMS m/z317([M+H] ⁺ ).

Example 5, Step 2: Preparation of 2-chloro-4-(pyridin-3-yl)-1H-imidazol-1-amine

To E-2-chloro-N-(4-chlorobenzylidene)-4-(pyridin-3-yl)-1H-imidazol-1-amine (210mg, 0.66mmol) in 2-methoxyethanol (5mL ) was added with 80% hydrazine hydrate (0.5 mL). The reaction mixture was heated to 130 °C for 1 hour, then the reaction mixture was concentrated. The residue was purified by column chromatography (petroleum ether:EtOAc, 1:1) to give the title compound (100 mg, 78%) as a yellow solid: ¹ HNMR (300 MHz, CDCl ₃ ) δ8.91 (s, 1H), 8.50 -8.49(m,1H),8.06-8.03(m,1H),7.43(s,1H),7.34-7.30(m,1H),4.87(br,2H); ESIMS m/z195([M+H] ⁺ ).

Example 5, Step 3: Preparation of N-(2-chloro-4-(pyridin-3-yl)-1H-imidazol-1-yl)acetamide (compound 39)

To a solution of 2-chloro-4-(pyridin-3-yl)-1H-imidazol-1-amine (30 mg, 0.15 mmol) and TEA (15 mg, 0.15 mmol) in DCM (5 mL) was added acetyl chloride at 0 °C (12 mg, 0.15 mmol). The reaction mixture was stirred at 0 °C for 30 minutes. The solvent was removed under reduced pressure and the residue was purified by prep-TLC (prep-TLC; petroleum ether:EtOAc, 1:2) to give the title compound (10 mg, 27%) as a yellow solid: mp129- 131°C; ¹ H NMR (300MHz, CDCl ₃ ) δ10.69(br,1H),8.81-8.80(m,1H),8.44-8.43(m,1H),8.02-8.00(m,1H),7.33( br s,2H),2.20(s,3H); ESIMS m/z237([M+H] ⁺ ).

Example 6, Step 1: Preparation of tert-butyl (4-bromo-1H-imidazol-1-yl)carbamate

Under nitrogen atmosphere, 4-bromo-1H-imidazole (3.2 g, 21.8 mmol) was weighed into a 500 mL round bottom flask equipped with a magnetic stir bar. Anhydrous DMF (12 mL) was added, and the mixture was placed on ice. After 10 minutes, the mixture was treated with NaH (0.840 g, 21.0 mmol. 60% dispersion in oil). After 5 minutes, the ice bath was removed, and the reaction mixture was allowed to warm to room temperature. After stirring vigorously for 15 minutes, return to the ice bath and add tert-butyl 3-(4-cyanophenyl)oxaziridine-2-carboxylate (1.92 g, 7.80 mmol). The reaction mixture was stirred vigorously for 5 minutes, then the ice bath was removed. After 5 min, the mixture was diluted with saturated NaHCO ₃ and extracted with EtOAc. _The organic phase was washed with dilute sodium carbonate, dried over _Na2SO4 , filtered and concentrated. The residue was purified by silica gel chromatography (0-5% MeOH/DCM) to give the title compound (1.16 g, 4.43 mmol, 57%) as a yellow oil: ¹ H NMR (400 MHz, CDCl ₃ ) δ 9.22 (s ,1H),7.36(d,J=1.5Hz,1H),6.97(d,J=1.5Hz,1H),1.48(s,9H); ESIMS m/z262([M] ⁺ ),260([M -2] ^- ).

Example 6, Step 2: Preparation of tert-butyl (4-bromo-1H-imidazol-1-yl)(ethyl)carbamate

Tert-butyl (4-bromo-1H-imidazol-1-yl)carbamate (1.16 g, 4.43 mmol) was dissolved in DMF (12 mL) and dispersed with NaH (0.310 g, 7.75 mmol, 60% in oil) body) processing. After 45 minutes, the mixture was cooled on an ice bath and treated with iodoethane (0.828 g, 5.31 mmol). After stirring for 5 minutes the ice bath was removed and the reaction mixture was stirred for an additional 90 minutes. The reaction mixture was diluted with anhydrous _K2CO3 (50 mL, 5% w _/ w), and the product was extracted with EtOAc. The organic phase _was washed with 5% anhydrous _K2CO3 and brine, dried _{over Na2SO4} and filtered. The organic layer was concentrated and the residue was purified by silica gel chromatography (0-10% MeOH/DCM) to give the title compound (1.023 g, 3.53 mmol, 80%) as a yellow oil: ¹ H NMR (400 MHz, CDCl ₃ )δ7.37(d, J=1.5Hz, 1H), 6.93(d, J=1.5Hz, 1H), 3.71(q, J=7.2Hz, 2H), 1.44(s, 9H), 1.16(t, J＝7.2Hz,3H); ESIMS m/z290([M+H] ⁺ ).

Example 6, Step 3: Preparation of tert-butyl ethyl(4-(pyridin-3-yl)-1H-imidazol-1-yl)carbamate (Compound 40)

(4-Bromo-1H-imidazol-1-yl)(ethyl)carbamate tert-butyl ester (253.7 mg, 0.874 mmol), pyridin-3-ylboronic acid (113 mg, 0.918 mmol), K ₂ CO ₃ ( 329 mg, 2.39 mmol), water (0.870 mL), anhydrous EtOH (1.74 mL), and toluene (3.50 mL) were placed in a 10 mL round bottom flask equipped with a condenser and a magnetic stir bar. The atmosphere was purged with nitrogen, and tetrakis(triphenylphosphine)palladium (30.0 mg, 0.026 mmol) was added. The mixture was heated to 110°C and stirred for 16 hours. The reaction mixture was cooled, the organic layer was set aside, and the aqueous layer was extracted with EtOAc. All organic phases were combined, dried over _Na2SO4 , filtered, and concentrated _. The residue was purified by silica gel chromatography (0-25% MeOH/DCM) to afford the title compound (81 mg, 0.28 mmol, 32%) as a yellow oil: ¹ H NMR (400 MHz, CD ₃ CN) δ 9.00 (d ,J=2.5Hz,1H),8.46(d,J=4.8Hz,1H),8.11(m,1H),7.67(d,J=1.3Hz,1H),7.61(d,J=1.2Hz,1H ),7.36(m,1H),3.76(q,J=7.1Hz,2H),1.45(s,9H),1.17(t,J=7.2Hz,3H); ESIMS m/z289([M+H] ⁺ ).

Example 6, Step 4: Preparation of tert-butyl (2-chloro-4-(pyridin-3-yl)-1H-imidazol-1-yl)(ethyl)carbamate (Compound 41)

Into a vacuum-dried 25 mL round bottom flask equipped with a magnetic stir bar and containing tert-butyl ethyl(4-(pyridin-3-yl)-1H-imidazol-1-yl)carbamate (77 mg, 0.267 mmol) Anhydrous THF (3 mL) was added and cooled to -78°C. n-Butyllithium (0.25 mL of 0.675 mmol, 2.5M in hexane) was added, and the mixture was stirred for 15 minutes. Hexachloroethane (189 mg, 0.80 mmol) dissolved in anhydrous THF (1 mL) was added dropwise to the reaction mixture while maintaining a temperature of -78 °C. After stirring for 1 hour, the reaction mixture was allowed to warm to room temperature. The reaction mixture was loaded directly onto a silica gel column and the THF was removed in a vacuum oven. The crude product was purified by silica gel chromatography (0-25% MeOH/DCM) to afford the title compound (3 mg, 0.009 mmol, 3.5%) as a yellow oil: ¹ H NMR (600 MHz, CDCl ₃ ) δ 8.92 (d, J＝1.6Hz, 1H), 8.50(dd, J＝4.8, 1.5Hz, 1H), 8.06(dt, J＝7.9, 2.0Hz, 1H), 7.33–7.27(m, 2H), 3.89(dq,J ＝14.5, 7.3Hz, 1H), 3.68(dq, J＝14.3, 7.2Hz, 1H), 1.44(s, 9H), 1.22(t, J＝7.2Hz, 3H); ¹³ C NMR (151MHz, CDCl ₃ )δ152.90,148.47,146.02,136.07,134.08,131.81,128.79,123.36,117.66,83.23,45.32,28.04,13.03; ESIMS m/z323([M+H] ⁺ ).

Example 7, Step 1: Preparation of tert-butyl (2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-yl)(prop-2-yn-1-yl)carbamate ( Compound 43)

To tert-butyl (2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-yl)carbamate (prepared as described in US20120110701A1; Garizi et.al.; 0.5 g, 1.823 mmol) in DMF (6.08 ml) was added sodium hydride (0.102 g, 2.55 mmol). The reaction mixture was stirred at 0 °C for 30 minutes, then propargyl bromide (0.325 g, 2.187 mmol, 80 wt.% in toluene) was added. The flask was warmed to ambient temperature, and the reaction mixture was stirred for 1 hour. Saturated ammonium chloride was added to the reaction mixture and the organic layer was extracted with ethyl acetate (3x). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel chromatography (0-20% methanol/dichloromethane) to afford the title compound as an orange oil (265 mg, 0.848 mmol, 46% yield): ¹ H NMR (300 MHz, CDCl ₃ ) δ8 .93(s,1H),8.46(s,1H),8.06(dt,J=7.9,1.9Hz,1H),7.33(s,1H),7.31-7.26(m,1H),4.62-4.46(m ,1H),4.46-4.27(m,1H),2.38(s,3H),2.37-2.36(m,1H),1.45(s,9H); ¹³ C NMR(101MHz,CDCl ₃ )δ159.88,152.57,147.96 ,146.54,146.48,135.68,132.00,129.75,123.51,123.48,114.96,83.90,74.38,27.99,12.17; ESIMS m/z313([M+H] ⁺ ).

Example 7, Step 2: Preparation of 2-methyl-N-(prop-2-yn-1-yl)-4-(pyridin-3-yl)-1H-imidazol-1-amine

To (2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-yl)(prop-2-yn-1-yl)carbamate tert-butyl ester (0.25g, 0.800mmol) in To a solution in dichloromethane (1 ml) was added 2,2,2-trifluoroacetic acid (0.981 ml, 12.81 mmol). The reaction mixture was stirred at ambient temperature for 3 hours. The reaction was quenched by addition of saturated sodium bicarbonate and the organic layer was extracted with dichloromethane (2x). The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford the title compound as a brown oil (168 mg, 0.792 mmol, 99% crude yield). The crude compound was used in subsequent reactions without further purification: ¹ H NMR (300 MHz, CDCl ₃ ) δ 8.90 (s, 1H), 8.41 (d, J=3.9 Hz, 1H), 8.02 (dt, J= 7.9,1.8Hz,1H),7.49(s,1H),7.26(dd,J=7.9,4.8Hz,1H),5.86(t,J=5.2Hz,1H),3.84(dd,J=5.2,2.4 Hz,2H),2.44(s,3H),2.41(t,J=2.4Hz,1H); ¹³ C NMR(75MHz,CDCl ₃ )δ147.51,146.48,146.28,134.99,131.88,130.41,123.48,115.28,79.47 ,74.21,42.18,12.28; ESIMS m/z213([M+H] ⁺ ).

Example 7, Step 3: Preparation of N-(2-methyl-4-(pyridin-3-yl)-1H-imidazol-1-yl)-3-(methylthio)-N-(propan-2 -alkyn-1-yl)butyramide (compound 42)

To 2-methyl-N-(prop-2-yn-1-yl)-4-(pyridin-3-yl)-1H-imidazol-1-amine (0.168g, 0.792mmol) in dichloromethane (3.17 ml) was added N-ethyl-N-isopropylpropan-2-amine (0.164ml, 0.950mmol) followed by 3-(methylthio)propionyl chloride (0.132g, 0.950mmol). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated and purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to afford the title compound as a yellow oil (30 mg, 0.095 mmol, 12% yield): ¹ H NMR (300 MHz, CDCl ₃ ) δ8.94(s,1H),8.50(d,J=3.8Hz,1H),8.07(dt,J=7.9,1.9Hz,1H),7.36(s,1H),7.31(dd,J= 7.6,4.6Hz,1H),4.75-4.66(m,1H),4.55-4.45(m,1H),2.77(t,J＝6.8Hz,2H),2.44(s,3H),2.37(s,1H ),2.34(br s,2H),2.04(s,3H); ¹³ C NMR(101MHz,CDCl ₃ )δ171.76,148.51,146.53,146.18,137.00,132.07,123.59,115.25,76.09,74.72,38.76,31.89, 28.87,28.06,15.96,12.31; ESIMS m/z315([M+H] ⁺ ).

Example A: Bioassay of green peach aphid (GREEN PEACH APHID, "GPA") (Myzus persicae) (MYZUPE).

GPA is the most important aphid pest of peach trees, causing reduced growth, shriveling of leaves and death of various tissues. It is also dangerous because it acts as a vector for the transport of plant viruses, such as potato virus Y and potato leafroll virus (for members of the nightshade/potato family Solanaceae), and various mosaic viruses (for many other grain crop). GPA attacks plants such as broccoli, burdock, cabbage, carrots, cauliflower, daikon, eggplant, kidney beans, lettuce, macadamia nuts, papaya, peppers, sweet potatoes, tomatoes, watercress, and zucchini, among others. GPA also attacks many ornamental crops such as carnations, chrysanthemums, flowering white cabbage, orangutan and roses. GPA has developed resistance to many insecticides.

Certain molecules disclosed herein were tested for GPA using the procedures described in the Examples below. In the reporting of the results, "Table 3: GPA (Peach Aphid) and sweetpotato whitefly-crawler (BEMITA) rating scale" (see Tables section) was used.

Cabbage seedlings (with 2-3 small (3-5 cm) true leaves) grown in 3 inch pots were used as test substrates. The seedlings were infested with 20-50 peach aphids (wingless adult and nymph stages) for 1 day before chemical application. Four pots with each seedling were used for each treatment. The test compound (2 mg) was dissolved in 2 mL of acetone/methanol (1:1) solvent to form a stock solution with a concentration of 1000 ppm test compound. The stock solution was diluted 5-fold with 0.025% Tween 20 in _H2O to obtain a solution of the test compound at a concentration of 200 ppm. The solution was sprayed onto both sides of the cabbage leaves using a hand-held aspirator-type sprayer until runoff formed. Control plants (solvent test) were sprayed with a diluent containing only 20% by volume acetone/methanol (1:1) solvent. The treated plants were kept in a nursery at about 25°C and ambient relative humidity (RH) for three days before being graded. Evaluation is performed by counting the number of live aphids per plant under a microscope. Percent control is measured by using Abbott's correction formula (WSA Abbott, "A Method of Computing the Effectiveness of an Insecticide" J. Econ. Entomol. 18 (1925), pp. 265-267) as follows.

Corrected percent control = 100*(X-Y)/X

in

X = number of live aphids on solvent-tested plants, and

Y = number of live aphids on treated plants

The results are shown in the table entitled "Table 4. Biological data of GPA (Peach aphid) and sweet potato whitefly crawler (B. sweetpotato)" (see Tables section).

Example B: Insecticidal Test of Sweet Potato Whitefly Crawler (Bemisia tabaci) (BEMITA) in a Leaf Spray Assay

Cotton plants (with 1 small (3-5 cm) true leaf) grown in 3 inch pots were used as test substrates. Plants were placed in a locus with whitefly adults. Adults are allowed to lay eggs for 2-3 days. After the 2-3 day spawning period, remove the plants from the adult whitefly sites. Adults were blown off the leaves using a hand-held Devilbiss sprayer (23 psi). Plants with egg infection (100-300 eggs per plant) were placed in a storage room at 82°F and 50% RH for 5-6 days for egg hatching and reptile stage development. For each treatment, four cotton plants were used. Compound (2 mg) was dissolved in 1 mL of acetone solvent to form a 2000 ppm stock solution. The stock solution was diluted 10 times with 0.025% Tween20/H ₂ O to obtain a 200 ppm test solution. The solution was sprayed onto both sides of the cotton leaves using a hand held Devilbiss sprayer until runoff. Reference plants (solvent detection) were sprayed with thinner only. Treated plants were stored in a storage room at about 82°F and 50% RH for 8-9 days prior to grading. Evaluation is performed by counting the number of live nymphs per plant under a microscope. Insecticidal activity was measured by using the Abbott correction formula and presented in "Table 4. Biological data of GPA (Peach aphid) and sweet potato whitefly crawler (Sweet potato whitefly)" (see column "Sweet potato whitefly"):

Corrected percent control = 100*(X-Y)/X

in

X = number of live nymphs on solvent-tested plants

Y = number of live nymphs on treated plants

Pesticidal acid addition salts, salt derivatives, solvates, ester derivatives, polymorphs, isotopic derivatives and radionuclide derivatives

Molecules of Formula 1 can be formulated as pesticidal acid addition salts. By way of non-limiting example, the amine functionality can form salts with the following acids: hydrochloric, hydrobromic, sulfuric, phosphoric, acetic, benzoic, citric, malonic, salicylic, malic, fumaric, oxalic , succinic acid, tartaric acid, lactic acid, gluconic acid, ascorbic acid, maleic acid, aspartic acid, benzenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, hydroxymethanesulfonic acid, and hydroxyethanesulfonic acid. Additionally, by way of non-limiting example, acid functional groups may form salts, including those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Examples of preferred cations include sodium cations, potassium cations and magnesium cations.

Molecules of Formula 1 may be formulated as salt derivatives. By way of non-limiting example, salt derivatives can be prepared by contacting the free base form with a sufficient amount of the desired acid, resulting in the salt. The free base form can be recovered by treating the salt with a suitable dilute aqueous base such as dilute aqueous sodium hydroxide (NaOH), dilute aqueous potassium carbonate, dilute aqueous ammonia and dilute aqueous sodium bicarbonate. As an example, in many cases a pesticide such as 2,4-D is made more water soluble by converting it to its dimethylamine salt.

Molecules of Formula 1 can be formulated to form stable complexes with solvent molecules that remain intact after non-complexed solvent molecules are removed from the compound. These complexes are often referred to as "solvates". However, it is particularly desirable to form stable hydrates with water as solvent molecule.

Molecules of Formula 1 may be formulated as ester derivatives. These ester derivatives can then be administered in the same manner as the invention disclosed herein.

Molecules of Formula 1 can be formulated as various crystalline polymorphs. Polymorphism is important in the development of pesticides because different crystalline polymorphs or structures of the same molecule can have very different physical and biological properties.

Molecules of formula 1 can be prepared with different isotopes. Of particular importance are molecules with ² H (also known as deuterium) instead of ¹ H.

Molecules of formula 1 can be prepared with different radionuclides. Of particular importance are molecules ^with14C .

Stereoisomers

Molecules of Formula 1 may exist as one or more stereoisomers. Accordingly, certain molecules may be prepared as racemic mixtures. It will be understood by those skilled in the art that one stereoisomer may be more active than the other. Individual stereoisomers may be obtained by known selective synthetic methods, conventional synthetic methods using resolved starting materials, or conventional resolution methods. Certain molecules disclosed herein can exist as two or more isomers. Various isomers include geometric isomers, diastereomers, and enantiomers. Accordingly, the molecules disclosed herein include geometric isomers, racemic mixtures, individual stereoisomers, and optically active mixtures. Those skilled in the art will recognize that one isomer may be more active than the other. For clarity, the structures disclosed in this disclosure are drawn in only one geometric form, but are intended to be representative of all geometric forms of the molecule.

combination

The molecules of formula 1 may also be used in combination with one or more compounds having acaricidal, algicidal, avicidal, bactericidal, fungicidal, herbicidal, insecticidal, molluscicidal, nematicidal, rodenticidal, or virucidal properties (eg, in a combined mixture, either administered simultaneously or sequentially). In addition, the molecule of formula 1 can also be used as anti-feeding agent, bird repellant, chemical biocide, herbicide safener, insect attractant, insect repellant, mammal repellent, mating disruptor, plant activator , plant growth regulator, or synergist compounds are used in combination (eg, in a combination mixture, either applied simultaneously or sequentially). Examples of such compounds in the above group that can be used with molecules of formula 1 are -(3-ethoxypropyl)mercury bromide, 1,2-dichloropropane, 1,3-dichloropropene, 1-methylcyclopropene, 1-naphthol, 2-(octylthio)ethanol, 2,3,5-tri-iodobenzoic acid, Caoyaping (2,3, 6-TBA), Caoyaping-dimethylammonium (2,3,6-TBA-dimethylammonium), Caoyaping-lithium (2,3,6-TBA-lithium), Caoyaping-potassium (2,3 ,6-TBA-potassium), Caoyaping-Na (2,3,6-TBA-sodium), 2,4,5-T (2,4,5-T), 2,4,5-T 2-Butoxypropyl (2,4,5-T-2-butoxypropyl), 2,4,5-T-2-ethylhexyl (2,4,5-T-2-ethylhexyl), 2, 4,5-T-3-butoxypropyl (2,4,5-T-3-butoxypropyl), 2,4,5-T-butyric acid (2,4,5-TB), 2,4, 5-T-butoxypropyl ester (2,4,5-T-butometyl), 2,4,5-T-butoxyethyl ester (2,4,5-T-butotyl), 2,4,5 -T-butyl (2,4,5-T-butyl), 2,4,5-T-isobutyl (2,4,5-T-isobutyl), 2,4,5-T-isooctyl Ester (2,4,5-T-isoctyl), 2,4,5-T-isopropyl (2,4,5-T-isopropyl), 2,4,5-T-methyl (2,4 ,5-T-methyl), 2,4,5-T-pentyl (2,4,5-T-pentyl), 2,4,5-T-sodium (2,4,5-T-sodium) , 2,4,5-T-triethylammonium (2,4,5-T-triethylammonium), 2,4,5-T-trolamine (2,4,5-T-trolamine), 2,4- Drop (2,4-D), 2,4-D-2-butoxypropyl (2,4-D-2-butoxypropyl), 2,4-D-2-ethylhexyl (2,4- D-2-ethylhexyl), 2,4-D-3-butoxypropyl (2,4-D-3-butoxypropyl), 2,4-D-ammonium (2,4-D-ammonium), 2 ,4-D butyric acid (2,4-DB), 2,4-D butyric acid-butyl (2,4-DB-butyl), 2,4-D butyric acid-dimethylammonium (2,4- DB-dimethylammonium), 2,4-butyric acid-isooctyl (2,4-DB-isoctyl), 2,4-butyric acid-potassium (2,4-D B-potassium), 2,4-D-butyric acid-sodium (2,4-DB-sodium), 2,4-D-butoxyethyl ester (2,4-D-butotyl), 2,4-D- Butyl (2,4-D-butyl), 2,4-D-diethylammonium (2,4-D-diethylammonium), 2,4-D-dimethylammonium (2,4-D-dimethylammonium), 2,4-D-diolamine (2,4-D-diolamine), 2,4-D-dodecylammonium (2,4-D-dodecylammonium), Saixin (2,4-DEB), Phosphate (2,4-DEP), 2,4-D-ethyl (2,4-D-ethyl), 2,4-D-heptylammonium (2,4-D-heptylammonium), 2, 4-D-isobutyl (2,4-D-isobutyl), 2,4-D-isooctyl (2,4-D-isoctyl), 2,4-D-isopropyl (2,4- D-isopropyl), 2,4-D-isopropylammonium (2,4-D-isopropylammonium), 2,4-D-lithium (2,4-D-lithium), 2,4-D-methyl Heptyl ester (2,4-D-meptyl), 2,4-D-methyl (2,4-D-methyl), 2,4-D-octyl (2,4-D-octyl), 2 ,4-drop-pentyl (2,4-D-pentyl), 2,4-drop-potassium (2,4-D-potassium), 2,4-drop-propyl (2,4-D-propyl ), 2,4-D-sodium (2,4-D-sodium), 2,4-D-glycoside (2,4-D-tefuryl), 2,4-D-tetradecyl ammonium ( 2,4-D-tetradecylammonium), 2,4-D-triethylammonium (2,4-D-triethylammonium), 2,4-D-tri(2-hydroxypropyl)ammonium (2,4-D- tris(2-hydroxypropyl)ammonium), 2,4-D-triethanolamine (2,4-D-trolamine), 2iP, 2-methoxyethylmercurychloride (2-methoxyethylmercurychloride), 2-phenylphenol (2-phenylphenol), 3,4-Dyramine (3,4-DA), 3,4-Dyrbutyric acid (3,4-DB), 3,4-Dyrpropionic acid (3,4-DP), 4-aminopyridine (4-aminopyridine), p-chlorophenoxyacetic acid (4-CPA), p-chlorophenoxyacetic acid-potassium (4-CPA-potassium), p-chlorophenoxyacetic acid-sodium (4-CPA-sodium) , chlorophenoxybutyric acid (4-CPB), chlorophenoxypropionic acid (4-CP P), 4-hydroxyphenethyl alcohol, 8-hydroxyquinoline sulfate, 8-phenylmercurioxyquinoline, abamectin, abscisic acid, ACC, Acephate, acequinocyl, acetamiprid, acethion, acetochlor, acetophos, acetoprole, acibenzolar , activated ester-S-methyl (acibenzolar-S-methyl), acifluorfen (acifluorfen), acifluorfen-methyl (acifluorfen-methyl), acifluorfen-sodium (acifluorfen-sodium ), aclonifen, acrep, acrithrin, acrolein, acrylonitrile, acypetacs, acypetacs-copper, acypetacs-zinc, alachlor, acetaminophen (alanycarb), albendazole, aldicarb, aldimorph, aldoxycarb, aldrin, allethrin , allicin, allidochlor, allosamidin, alloxydim, alloxydim-sodium, allyl alcohol, allyxycarb, alorac, alpha-cypermethrin, alpha-endosulfan, ametoctradin, ametridione , ametryn, ambuzin, amicarbazone, amicarthiazol, amidithion, amidoflumet, amidosulfuron, Aminocarb, aminocyclopyrachlor, aminocyclopyrachlor, aminocyclopyrachlor yclopyrachlor-methyl), aminocyclopyrachlor-potassium, aminopyralid, aminopyralid-potassium, aminopyralid-tris(2-hydroxypropyl) Ammonium (aminopyralid-tris (2-hydroxypropyl) ammonium), amiprofos-methyl, amiprophos, amisulbrom, amiton, amiprophos Amiton oxalate, amitraz, amitrole, ammonium sulfamate, ammoniumα-naphthaleneacetate, amobam, 1 - Ampropylfos, anabasine, ancymidol, anilazine, anilofos, anisuron, anthraquinone , antu, apholate, aramite, arsenous oxide, asomate, aspirin, asulam, asulam- Potassium (asulam-potassium), asulam-sodium (asulam-sodium), athidathion, atraton, atrazine, aureofungin, aviglycine , aviglycine hydrochloride, azaconazole, azadirachtin, azafenidin, azamethiphos, azimsulfuron, cottonphos ( azinphos-ethyl), azinphos-methyl, aziprotryne, azithiram, azobenzene, azocyclotin, azothoate, azithromycin Esters (azoxystrobin), bachmedesh, oat spirit (barban), barium hexafluorosilicate (barium hexafluorosil icate), barium polysulfide, barthrin, BCPC, beflubutamid, benalaxyl, benalaxyl-M, benalaxyl ( benazolin), benazolin-dimethylammonium, benazolin-ethyl, benazolin-potassium, bencarbazone, benclothiaz, bendiocarb, benfluralin, benfuracarb, benfuresate, benodanil, benomyl, benoxacor, benoxafos ), benquinox, bensulfuron, bensulfuron-methyl, bensulide, bensultap, bentaluron, bentazone (bentazone), bentazone-sodium, benthiavalicarb, benthiavalicarb-isopropyl, benthiazole, bentranil ), benzadox, benzadox-ammonium, benzalkonium chloride, benzamacril, benzamacril-isobutyl ester, benzamorf, benzfendizone, benzalkon Benzipram, benzobicyclon, benzofenap, benzofluor, benzohydroxamicacid, benzoximate, benzoylprop , benzoylprop-ethyl, benzthiazuron, benzyl benzoate, benzyl adenine, berberine, berberine chloride ), β-cyfluthrin (beta-cyfluthri n), β-cypermethrin, bethoxazin, bicyclopyrone, bifenazate, bifenox, bifenthrin, pyriflux Ester (bifujunzhi), bialafos (bilanafos), bialafos-sodium (bilanafos-sodium), music killing mite (binapacryl), disease cyanide (bingqingxiao), biological allethrin (bioallethrin), bioethrin, biopermethrin, bioresmethrin, biphenyl, bisazir, bismerthiazol, bispyribac, bispyrrole Bispyribac-sodium, bistrifluron, bitertanol, bithionol, bixafen, blasticidin-S, borax, Bordeaux mixture, boricacid, boscalid, brassinolide, brassinolide-ethyl, bark beetle sex pheromone (brevicomin) , brodifacoum, brofenvalerate, brofluthrinate, bromacil, bromacil-lithium, bromacil-sodium, bromadiolone, bromethalin, bromethrin, bromfenvinfos, bromoacetamide, bromobonil, bromobutyramid (bromobutide), bromocyclen, bromo-DDT (bromo-DDT), bromofenoxim, bromophos, bromophos-ethyl, bromofen ( bromopropylate), bromothalonil (bromothalonil), bromoxynil (bromoxynil), butyryl bromoxynil (bromoxynilbutyrat e), bromoxynil heptanoate, bromoxyniloctanoate, bromoxynil-potassium, brompyrazon, bromuconazole, bronopol (bronopol), bucarpolate, bufencarb, buminafos, bupirimate, buprofezin, Burgundy mixture, busulfan (busulfan), butacarb, butachlor, butafenacil, butamifos, butathiofos, butenachlor, Butethrin, Buthidazole, Buthiobate, Buthiuron, Butocarboxim, Butonate, Butopyronoxyl, Butanone Butoxycarboxim, butralin, butroxydim, buturon, butylamine, butyrate, cacodylic acid, cadusafos , cafenstrole, calcium arsenate, calcium chlorate, calcium cyanamide, calcium polysulfide, calvinphos, gram chlorate Cambendichlor, camphechlor, camphor, captafol, captan, carbamorph, carbonolate, carbaryl ( carbaryl), carbasulam, carbendazim, carbendazim benzenesulfonate, carbendazim sulfite, carbetamide, carbofuran (carbofuran), carbon disulfide (carbon disulfide), carbon tetrachloride, trithion phosphorus (carbophen othion), carbosulfan, carboxazole, carboxide, carboxin, carfentrazone, carfentrazone-B Carfentrazone-ethyl, carpropamid, cartap, cartap hydrochloride, carvacrol, carvone, CDEA, Cellocidin, CEPC, ceralure, Cheshunt mixture, chinomethionat, chitosan, chlobenthiazone, chlomethoxyfen, chloral Chloralose, chloramben, chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben Chloramben-methylammonium, chloramben-sodium, chloramine phosphor, chloramphenicol, chloraniformethan, chloranil, butyryl Chloranocryl, Chlorantraniliprole, Chlorazifop, Chlorazifop-propargyl, Chlorazine, Chlorbenside, Diflubenzuron (chlorbenzuron), borneol (chlorbicyclen), chlorobromuron (chlorbromuron), chloralkyne spirit (chlorbufam), chlordane (chlordane), chlordecone (chlordecone), chlordimeform (chlordimeform), chlordimeform hydrochloride ( chlordimeformhydrochloride), chlorempenthrin, chlorethoxyfos, chloreturon, chlorfenac, chlorfenac-ammonium ), Chlorfenac-sodium, Chlorfenapyr, Chlorfenazole, Chlorfenethol, Chlorfenprop, Chlorfenson, Dimiten (chlorfensulphide), chlorfenvinphos, chlorfluazuron, chlorflurazole, chlorfluren, Chlorfluren-methyl ester, chlorflurenol, chlorflurenol-methyl, chlorflurenol Chloridazon, chlorimuron-methyl deethylate (chlorimuron), chlorimuron-ethyl, chlormephos, chlormequat, chlormequat chloride, Chlornidine, chlornitrofen, chlorobenzilate, chlorodinitronaphthalenes, chloroform, chloromebuform, chloromethiuron, chloroanisole (chloroneb), chlorophacinone, chlorophacinone-sodium, chloropicrin, chloropon, chloropropylate, chlorothalonil, Chlorotoluron, Chloroxuron, Chloroxynil, Chlorphonium, Chlorphonium Chloride, Chlorphoxim, Chlorprazophos, chlorprocarb, chlorpropham, chlorpyrifos, chlorpyrifos-methyl, chlorquinox, chlorsulfuron , chlorophthalic acid (chlorthal), chlorophthalic acid - dimethyl (chlorthal-dimethyl), chlorophthalic acid - a methyl (chlorthal hal-monomethyl), chlorthiamid, chlorthiophos, chlozolinate, choline chloride, chromafenozide, cinerin I I), cinerin II, cinerins, cinidon-ethyl, cinmethylin, cinosulfuron, ciobutide, trimetrione (cisanilide), cismethrin, clethodim, climbazole, cliodinate, clodinafop, clodinafop-propargyl (clodinafop-propargyl), cloethocarb, clofencet, clofencet-potassium, clofentezine, clofibric acid, clofop, clofop-isobutyl -isobutyl), clomazone, clomeprop, cloprop, cloproxydim, clopyralid, clopyralid-methyl ester (clopyralid-methyl), clopyralid-olamine, clopyralid-potassium, clopyralid-tris (2-hydroxypropyl) ammonium (clopyralid-tris ( 2-hydroxypropyl)ammonium), cloquintocet, cloquintocet-mexyl, cloransulam, cloransulam-methyl, closantel, clothianidin, clotrimazole, seat cloxyfonac, cloxyfonac-sodium, CMA, codlelure, colophonate, copper acetate, copper acetoarsenite, copper arsenate, basic Copper carbonate (basic), copper hydroxide, copper naphthene carboxylate (copp ernaphthenate), copper oleate, copper oxychloride, copper silicate, copper sulfate, copper zinc chromate, coumachlor, coumafuryl, fly poison Phosphorus (coumaphos), coumatetralyl, coumithoate, coumoxystrobin, CPMC, CPMF, CPPC, credazine, Cresol, crimidine, crotamiton, crotoxyphos, crufomate, cryolite, cue-lure ), cufraneb, cumyluron, cuprobam, cuprousoxide, curcumenol, cyanamide, cyanatryn, cyanazine (cyanazine), cyanofenphos, cyanophos, cyanthoate, cyanraniliprole, cyazofamid, cybutryne, cyclafuramid, cyclanilide ), cyclethrin, cycloate, cycloheximide, cycloprate, cycloprothrin, cyclosulfamuron, thiophene Cycloxydim, cycluron, cyenopyrafen, cyflufenamid, cyflumetofen, cyfluthrin, cyhalofop, cyhalofop- Butyl (cyhalofop-butyl), cyhalothrin (cyhalothrin), tricyclic tin (cyhexatin), cymiazole, cymiazole hydrochloride, cymoxanil, cyometrinil ( cypendazole), cypermethrin, cyperquat, cyperquat chloride, phenyl ether Cyphenothrin, cyprazine, cyprazole, cyproconazole, cyprodinil, cyprofuram, cyprofuram (cypromid), cyprosulfamide, cyromazine, cythioate, daimuron, dalapon, dalapon-calcium, dalapon-magnesium ), dalapon-sodium, daminozide, dayoutong, dazomet, dazomet-sodium, dibromochloropropane (DBCP), d-camphor, dichloroisopropyl ether (DCIP), production-increasing amine (DCPTA), DDT (DDT), debacarb, decafentin, decarbofuran, dehydroacetic acid ( dehydroacetic acid), delachlor, deltamethrin, demephion, demephion-O, demephion-S, Demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S( demeton-S), demeton-S-methyl, demeton-S-methylsulphon, demeton-S-methylsulphon, desmedipham, desmethyn, dextro-trans chlorine D-fanshiluquebingjuzhi, diafenthiuron, dialifos, di-allate, diamidafos, diatomaceous earth, diazinon ), dibutyl phthalate, dibutyl succinate, dicamba, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba -dicamba-diolamine, dicamba-isopropylammonium (dicamba-isopropylammonium), dicamba -Dicamba-methyl, dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-trolamine , dicapthon, dichlobenil, dichlofenthion, dichlofluanid, dichlorone, dichloralurea, dichlorbenzuron , dichlorflurenol, dichlorflurenol-methyl ester, dichlormate, dichlormid, dichlorophen, 2,4-dichlorprop, 2,4-dichlorprop- 2-ethylhexyl (dichlorprop-2-ethylhexyl), 2,4-dichlorprop-butoxyethyl ester (dichlorprop-butotyl), 2,4-dichlorprop-dimethylammonium (dichlorprop-dimethylammonium), 2 ,4-Dichlorprop-ethylammonium, 2,4-Dichlorprop-isoctyl, 2,4-Dichlorprop-methyl, Ethyl 2 ,4-Dichlorprop-P, Dichlorprop-P-2-ethylhexyl, Dichlorprop-P, Dichlorprop-P -P-dimethylammonium), 2,4-dichlorprop-potassium, 2,4-dichlorprop-sodium, dichlorvos, dichlorozoline, benzyl chloride Diclobutrazol, diclocymet, diclofop, diclofop-methyl, diclomezine, diclomezine-sodium sodium), dicloran, diclosulam, dicofol, dicoumarol, N-(3-methylphenyl) methyl carbamate (dicresyl), Phosphorus (d icrotophos), dicyclanil, dicyclonon, dieldrin, dienochlor, diethamquat, diethamquat dichloride, metolachlor (diethatyl), methachlor-ethyl (diethyl-ethyl), diethofencarb, dietholate, diethylpyrocarbonate, diethyltoluamide, difenacoum, benzene Difenoconazole, Difenopenten, Difenopenten-ethyl, Difenoxuron, Difenzoquat, Difenacyl methylsulfate Difenzoquat metilsulfate, difethialone, diflovidazin, diflubenzuron, diflufenican, diflufenzopyr, diflufenzopyr-sodium , diflumetorim, dikegulac, dikegulac-sodium, dilor, dimatif, dimefluthrin, methylflu Dimefox, Dimefuron, Dimepiperate, Dimetachlone, Dimetan, Dimethacarb, Dimethachlor, Pentazine (dimethametryn), dimethenamid, dimethenamid-P, dimethipin, dimethirimol, dimethoate, dimethimorph (dimethomorph), dimethrin, dimethylcarbate, dimethyl phthalate, dimethylvinphos, dimetilan, dimexano, dimeth Dimidazon, Dimox ystrobin), dinex, dinex-diclexine, dingjunezuo, diniconazole, R-diniconazole-M, dinitramine, Xiaomite (dinobuton), dinocap, dinocap-4, dinocap-6, dinocton, dinofenate, nipentyl (dinopenton), dinoprop, dinosam, dinoseb, dinoseb acetate, dinoseb-ammonium, dinoseb - dinoseb-diolamine, dinoseb-sodium, dinoseb-trolamine, dinosulfon, dinotefuran, dinoterb, tetrol Dinoterb acetate, dinoterbon, diofenolan, dioxabenzofos, dioxacarb, dioxathion, diphacinone, Diphacinone-sodium, diphenamid, diphenylsulfone, diphenylamine, dipropalin, dipropetryn, dipyrithione, diquat Diquat, diquatdibromide, disparlure, 2,4-sodium disulfide (disul), disulfiram, disulfoton, 2, 4-sodium disulfide (disul-sodium), ditalimfos, dithianon, dithicrofos, dithioether, dithiopyr, diquat Diuron, d-limonene, DMPA, DNOC, DNOC-ammonium, DNOC-potassium (DNOC- potassium), dinitrocresol-sodium (DNOC-sodium), dodemorph, dodemorph acetate ( dodemorphacetate), dodemorph benzoate, dodicin, dodicin hydrochloride, dodicin-sodium, dodicin ( dodine), dofenapyn, dominicalure, doramectin, drazoxolon, DSMA, dufulin, EBEP, EBP, ecdysterone ( ecdysterone), edifenphos, eglinazine, eglinazine-ethyl, emamectin, emamectin benzoate ), EMPC, empenthrin, endosulfan, endothal, endothal-diammonium, endothal-dipotassium (endothal-dipotassium), endothal-disodium, endothion, endrin, enestroburin, fenthion (EPN), epocholeone, epofenonane , epoxiconazole, eprinomectin, epronaz, EPTC, erbon, ergocalciferol, dichlorohexanoyl Erlujixiancaoan, esdépalléthrine, S-fenvalerate, esprocarb, etacelasil, etaconazole, etaphos, etem, ethaboxam (ethaboxam), ethachlor, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethaprochlor, ethylene Ethephon, ethidimuron, ethiofencarb, ethiolate, ethion, ethizone ozin), ethiprole, ethirimol, ethoate-methyl, ethofumesate, etohexadiol, ethoprophos, chlorofluoro Ethoxyfen, Ethoxyfen-ethyl, Ethoxyquin, Ethoxysulfuron, Ethychlozate, Ethyl formate , α-naphthalene ethyl acetate, ethyl-DDD, ethylene, dibromoethylene, dichloroethylene, ethylene oxide, ethylicin, 2,3-dihydroxypropyl thiolated ethyl Mercury (ethylmercury2,3-dihydroxypropyl mercaptide), ethylmercury acetate, ethylmercury bromide, ethylmercury chloride, ethylmercury phosphate, nitrate etinofen, etnipromid, etnipromid, etofenprox, etoxazole, etridiazole, etrimfos , Eugenol (eugenol), Caobisan (EXD), famoxadone, famphur, fenamidone, fenaminosulf, fenamiphos, Fenapanil, fenarimol, fenasulam, fenazaflor, fenazaquin, fenbuconazole, fenbutatin oxide ), fenchlorazole, fenchlorazole-ethyl, fenchlorphos, fenclorim, fenethacarb, fenfluthrin , fenfuram, fenhexamid, fenitropan, fenitrothion, fenjuntong, secbutacarb (f enobucarb), 2,4,5-fenoprop, 2,4,5-fenoprop-3-butoxypropyl, 2,4,5-fenoprop -butoxypropyl ester (fenoprop-butometyl), 2,4,5-nylpropionic acid-butoxyethyl ester (fenoprop-butotyl), 2,4,5-nylpropionic acid-butyl (fenoprop-butyl) , 2,4,5-(fenoprop-isoctyl), 2,4,5-(fenoprop-methyl), 2,4,5-(fenoprop-isoctyl), 2,4,5-( Fenoprop-potassium), Fenothiocarb, Fenoxacrim, Fenoxanil, Fenoxaprop, Fenoxaprop-ethyl, Fenoxaprop-ethyl (fenoxaprop-P), fenoxaprop-P-ethyl, fenoxasulfone, fenoxycarb, fenpiclonil, fenpirithrin , fenpropathrin, fenpropidin, fenpropimorph, fenpyrazamine, fenpyroximate, fenridazon, fenridazon-potassium, fenridazon-propyl ester, fenpyroximate (fenson) , fensulfothion, fenteracol, fenthiaprop, fenthiaprop-ethyl, fenthion, fenthion-ethyl (fenthion-ethyl), fentin, fentin acetate, fentin chloride, fentin hydroxide, fentrazamide, Fentrifanil, fenuron, fenuronTCA, fenvalerate, ferbam, ferimzone, ferrous sulfate ), fipronil (fipronil), wheat straw fluorine (flamprop), wheat straw fluoride isopropyl ester (flam prop-isopropyl), flamprop-M, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl , flazasulfuron, flocoumafen, flometoquin, flonicamid, florasulam, fluacrypyrim, fluazifop , fluazifop-butyl, fluazifop-methyl, fluazifop-methyl, fluazifop-P, fluazifop-butyl (fluazifop-P-butyl), fluazinam, fluazolate, fluazuron, flubendiamide, flubenzimine, flucarbazone ( flucarbazone), flucarbazone-sodium, flucetosulfuron, fluchloralin, flucofuron, flucycloxuron, flucyfenol flucythrinate, fludioxonil, fluenetil, fluensulfone, flufenacet, flufenerim, flufenican, flufenoxuron, fluproxil flufenprox, flufenpyr, flufenpyr-ethyl, flufiprole, flumethrin, flumetover, flumethrin (flumetralin), flumetsulam, flumezin, flumiclorac, flumiclorac-pentyl, flumioxazin, alkyne flumipropyn, flumorph, fluometuron, fluopicolide, fluopyram, fluorbenside, Fluoridamid, fluoroacetamide, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, fluoroimide ( fluoroimide), fluoromidine, fluoronitrofen, fluothiuron, fluotrimazole, fluoxastrobin, flupoxam, flupropacil, Flupropadine, flupropanate, flupropanate-sodium, flupyradifurone, flupyrsulfuron, flupyrsulfuron- methyl), flupyrsulfuron-methyl-sodium, fluquinconazole, flurazole, flurenol, flurenol-butyl, Flurenol-methyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr -butometyl), fluroxypyr-meptyl, flurprimidol, flursulamid, flurtamone, flusilazole, sulfur Flusulfamide, fluthiacet, fluthiacet-methyl, flutianil, flutolanil, flutriafol, fluamide Fluvalinate, Fluxapyroxad, Fluxofenim, Folpet, Fomesafen, Fomesafen-sodium, Fomesafen-sodium Fonofos, foramsulfuron, forchlorfenuron, formaldehyde, formaldehyde etanate), formetanate hydrochloride, formothion, formparanate, formparanate hydrochloride, fosamine, woodphos-ammonium (fosamine-ammonium), fosetyl, fosetyl-aluminium, fosmethilan, chlorpyrifos-methyl (fospirate), fosthiazate, fenthion (fosthietan), frontalin, fuberidazole, fucaojing, fucaomi, funaihecaoling, fuphenthiourea, furalane, furalaxyl ( furalaxyl, furamethrin, furametpyr, furathiocarb, furcarbanil, furconazole, furconazole-cis, furfural Furethrin, furfural, furilazole, furmecyclox, furophanate, furyloxyfen, beta-cyhalothrin (gamma-cyhalothrin), γ-666 (γ-HCH), genit, gibberellic acid, gibberellins, gliftor, glufosinate ), glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium , glyodin, glyoxime, glyphosate, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate -isopropylammonium (glyphosate-isopropylammonium), glyphosate-monoammonium (glyphosate-monoammonium), Glyphosate-potassium (glyphosate-potassium), glyphosate-sesquisodium (glyphosate-sesquisodium) gossyplure), grandlure, griseofulvin, guazatine, guazatine acetates, halacrinate, halfenprox , halofenozide, halosafen, halosulfuron, halosulfuron-methyl, haloxydine, fluorine Haloxyfop, haloxyfop-etotyl, haloxyfop-methyl, haloxyfop-P, haloxyfop-P -etotyl), haloxyfop-P-methyl, haloxyfop-sodium, HCH, hemel, hempa , dieldrin (HEOD), heptachlor, heptenophos, heptopargil, heterophos, hexachloroacetone, hexachlorobenzene, six Hexachlorobutadiene, hexachlorophene, hexaconazole, hexaflumuron, hexaflurate, hexalure, hexamide, cyclozine Hexazinone, hexylthiofos, hexythiazox, aldrin (HHDN), holosulf, huancaiwo, huangcaoling, huanjunzuo, hydramethylnon , hydrargaphen, hydrated lime, hydrogen cyanide, hydroprene, hymexazol, hyquincarb, indole acetic acid (IAA), indole butyric acid (IBA), icaridin, imazalil, imazalil nitrate, imazalil Imazalil sulfate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, formazan imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imidazoquine imazaquin-ammonium, imazaquin-methyl, imazaquin-sodium, imazethapyr, imazethapyr-ammonium, azole Imazosulfuron, imibenconazole, imicyafos, imidacloprid, imidaclothiz, iminoctadine, iminoctadine ( iminoctadinetriacetate), iminoctadine trialbesilate, imiprothrin, inabenfide, indanofan, indaziflam, indoxacarb, benzoin Inezin, iodobonil, iodocarb, iodomethane, iodosulfuron-methyl, iodosulfuron-methyl, iodosulfuron-methyl -sodium), iofensulfuron, iofensulfuron-sodium, ioxynil, ioxynil octanoate, ioxynil-lithium, ioxynil-sodium, Ipazine, ipconazole, ipfencar bazone), iprobenfos, iprodione, iprovalicarb, iprymidam, ipsdienol, ipsenol , IPSP, isamidofos, isazofos, isobenzan, isocarbamid, isocarbophos, isocil, isoaldrin (isodrin), isofenphos, isofenphos-methyl, isolan, isomethiozin, isonoruron, nitrogen isopolinate, isoprocarb, isopropalin, isoprothiolane, isoproturon, isopyrazam, isopyrimol, isothioate ), isotianil, isouron, isovaledione, isoxaben, isoxachlortole, isoxadifen, isoxadifen-ethyl ester, Isoxaflutole, isoxapyrifop, isoxathion, ivermectin, izopamfos, japonilure, japothrins, japonilure Inulin I (jasmolin I), jasmolin II (jasmonic acid), mesulfazone (jiahuangchongzong), methyl synergistic phosphorus (jiajizengxiaolin), melystrobin (jiaxiangjunzhi), Jiecaowan, jiecaoxi, jodfenphos, juvenile hormone I, juvenile hormone II, juvenile hormone III, thiophene kadethrin, karbutilate, karetazan, karetazan-potassium, kasugamycin, kasugamycin hydrochloride, kejunlin, kelevan ), ketospiradox, ketospiradox-potassium, kinetin, kinoprene, kresoxim-methyl, kuicaoxi, lactofen, high-efficiency Lambda-cyhalothrin, latilure, lead arsenate, lenacil, lepimectin, leptophos, lindane, lineatin, linuron , acetamiphos (lirimfos), l itlure, looplure, lufenuron (lufenuron) Maleic hydrazide, malonoben, maltodextrin, MAMA, mancopper, mancozeb , mandipropamid (mandipropamid), maneb (maneb), matrine (matrine), azide phosphorus (mazidox), 2 methyl 4 chlorine (MCPA), 2 methyl 4 chloro-2-ethylhexyl ( MCPA-2-ethylhexyl), 2 methyl 4 chloro-butoxy ethyl ester (MCPA-butotyl), 2 methyl 4 chloro-butyl (MCPA-butyl), 2 methyl 4 chloro-dimethylammonium (MCPA-dimethylammonium), 2 methyl 4 chloro-diolamine (MCPA-diolamine), 2 methyl 4 chloro-ethyl (MCPA-ethyl), 2 methyl 4 chloro-isobutyl (MCPA-isobutyl), 2 methyl 4 chloro-isooctyl ( MCPA-isoctyl), 2 methyl 4 chloro-isopropyl (MCPA-isopropyl), 2 methyl 4 chloro-methyl (MCPA-methyl), 2 methyl 4 chloro-alcohol amine (MCPA-olamine), 2 methyl 4 chloro- Potassium (MCPA-potassium), MCPA-sodium (MCPA-sodium), MCPA-thioethyl, MCPA-trolamine, 2-methyl-4-chlorobutyl MCPB, MCPB-ethyl, MCPB-methyl, MCPB-sodium, ortho Mebenil, mecarbam, mecarbinzid, mecarphon, mecoprop, mecoprop-2-ethylhexyl -2-ethylhexyl), mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-dimethylammonium Octyl ester (mecoprop-isoctyl), mecoprop-methyl, refined mecoprop -P), mecoprop-P-2-ethylhexyl (mecoprop-P-2-ethylhexyl), mecoprop-P-dimethylammonium, mecoprop-P-dimethylammonium Mecoprop-P-isobutyl, mecoprop-potassium, mecoprop-P-potassium, mecoprop-potassium Mecoprop-sodium, mecoprop-trolamine, medimeform, medinoterb, medinoterb acetate, Medlure, mefenacet, mefenpyr, mefenpyr-diethyl, mefluidide, mefluidide-diolamine, mefluidide - Mefluidide-potassium, megatomoic acid, menazon, mepanipyrim, meperfluthrin, mephenate, mephosfolan, mepiquat, mepiquat chloride ), mepiquat pentaborate, mepronil, meptyldinocap, mercuric chloride, mercuric oxide, mercurous chloride, merphos , mesoprazine, mesosulfuron, mesosulfuron-methyl, mesotrione, mesulfen, mesulfenfos ), metaflumizone, metalaxyl, metalaxyl-M, metalaldehyde, metam, metam-ammonium ammonium), metamifop, metamitron, metam-potassium, metam-sodium, meme tazachlor), metazosulfuron, metazoxolon, metconazole, metepa, metflurazon, methylbenzothiuron ( methabenzthiazuron), methacrifos, methalpropalin, methamidophos, methasulfocarb, methazole, methfuroxam, methaphos ( methidathion), methiobencarb, methiocarb, methiopyrisulfuron, methiotepa, methiozolin, methiuron, Methocrotophos, Metometon, Methomyl, Methoprene, Methoprotryne, Methoquin-butyl, Methothrin ( methoxychlor, methoxyfenozide, methoxyphenone, methyl apholate, methyl bromide, methyleugenol, methyl Iodine, methyl isothiocyanate, methylacetophos, methylchloroform, methyldymron, methylene chloride, methylmercury benzoate , methylmercurydicyandiamide, methylmercury pentachlorophenoxide, methylneodecanamide, metiram, metobenzuron, metobromuron, Metofluthrin, metolachlor, metolcarb, metominostrobin, metosulam, metoxadiazone ), metoxuron, metrafenone, metribuzin, metsulfovax, metsulfuron, metsulfuron-methyl, Mevinphos, mexacarbate, mieshuan, milbemectin, milbemycin oxime, milneb, mipafox, Mirex, MNAF, moguchun, molinate, molosultap, monalide, monisouron, monochloroacetic acid, monoclonal Monocrotophos, monolinuron, monosulfuron, monosulfuron-ester, monuron, monuron TCA (monuron TCA), cutting grass ( morfamquat), morfamquat dichloride, moroxydine, moroxydine hydrochloride, morphothion, morzid, moxidectin, formazine Sodium (MSMA), muscalure, myclobutanil, myclozolin, N-(ethylmercury)-p-toluenesulphonanilide, Nabam, Naftalofos, Naled, Naphthalene, Naphthaleneacetamide, Naphthalic anhydride, Naphthoxyacetic acids, Naproanilide, Napropamide, naptalam, naptalam-sodium, natamycin, neburon, niclosamide, spironamide - niclosamide-olamine, nicosulfuron, nicotine, nifluridide ), nipyraclofen, nitenpyram, nithiazine, nitralin, nitrapyrin, nitrilacarb, Nitrofen, nitrofluorfen, nitrostyrene, nitrothal-isopropyl, norbormide, norflurazon, nornicotine ), noruron, novaluron, noviflumuron, nuarimol, OCH, octachlorodipropyl ether, octhilinone, Ofurace, omethoate, orbencarb, orfralure, o-dichlorobenzene, orthosulfamuron, oryctalure, orysastrobin, amisulfame ( oryzalin), osthol, ostramone, oxabetrinil, oxadiargyl, oxadiazon, oxadixyl, oxamate, Oxamyl, oxapyrazon, oxapyrazon-dimolamine, oxapyrazon-sodium, oxasulfuron, oxaziclomefone, quinoline Copper (oxine-copper), oxolinic acid, oxpoconazole, oxpoconazole fumarate, oxycarboxin, oxydemeton-methyl, iso Oxydeprofos, oxydisulfoton, oxyfluorfen, oxymatrine, oxytetracycline, oxytetracycline hydrochloride, paclobutrazol (paclobutrazol), paichongding (paichongding), p-dichlorobenzene, p-furone ( parafluron), paraquat, paraquat dichloride, paraquat dimethilsulfate, parathion, parathion-methyl, chlorobenzene Pyridine (parinol), pebulate, pefurazoate, pelargonic acid, penconazole, pencycuron, pendimethalin, pendimethalin Penflufen, penfluron, penoxsulam, pentachlorophenol, pentanochlor, penthiopyrad, cypermethrin (pentmethrin), pentoxazone, perfluidone, permethrin, pethoxamid, phenamacril, phenazine oxide, cotton Phenisopham, phenkapton, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenothrin, phenproxide ), phenthoate, phenylmercuriurea, phenylmercury acetate, phenylmercury chloride, phenylmercury derivative of catechol pyrocatechol), phenylmercury nitrate, phenylmercury salicylate, phorate, phosacetim, phosalone, phosdiphen ), phosfolan, phosfolan-methyl, phosglycin, phosmet, phosnichlor, phosphamidon , Phosphine (phosphine), Eprofocarb ( Phosphocarb), phosphorus, phostin, phoxim, phoxim-methyl, phthalide, picloram, amiloride Acid-2-ethylhexyl (picloram-2-ethylhexyl), amilopyral acid-isooctyl (picloram-isoctyl), amilopyral acid-methyl (picloram-methyl), amilopyral acid-olamine ( picloram-olamine), picloram-potassium, picloram-triethylammonium, picloram-triethylammonium, picloram-tris( 2-hydroxypropyl)ammonium), picolinafen, picoxystrobin, pindone, pindone-sodium, pinoxaden, peripril Piperalin, piperonyl butoxide, piperonyl cyclone, piperophos, piproctanyl, piproctanyl bromide, piprotal , pirimaphos, pirimicarb, pirimioxyphos, pirimiphos-ethyl, pirimiphos-methyl, plifenate, Polycarbamate, polyoxins, polyoxorim, polyoxorim-zinc, polythialan, potassium arsenite ), potassium azide, potassium cyanate, potassium gibberellic acid, potassium naphthenate (potassium naphthenate), potassium polysulfide (potassium polysulfide), potassium thiocyanate, potassium α-naphthalene acetate, pp'-DDT, dextro prallethrin, precocene I, precocene II, precocene III, pretilachlor, primidop hos), primisulfuron, primisulfuron-methyl, probenazole, prochloraz, prochloraz-manganese , proclonol, procyazine, procymidone, prodiamine, profenofos, profluazol, ciproflurazine ( profluralin), profluthrin, profoxydim, proglinazine, proglinazine-ethyl, prohexadione, prohexadione-calcium, prohydrojasmon, promacyl, promecarb, prometon, prometryn, promurit, propachlor, propamidine, prohydrojasmon Propamidine dihydrochloride, propamocarb, propamocarb hydrochloride, propanil, propaphos, propaquizafop, fast mite Propargite, Proparthrin, Propazine, Propetamphos, Propham, Propiconazole, Propineb, Promethazol Propisochlor, propoxur, propoxycarbazone, propoxycarbazone-sodium, propylisome, propyrisulfuron, benzoyl Propyzamide, Proquinazid, Prosulactone, Prosulfalin, Prosulfocarb, Prosulfuron, Ethiazole Phosphorus (prothidathion), thiocarb (prothiocarb) , prothiocarb hydrochloride, prothioconazole, prothiofos, prothoate, protrifenbute, proxan, proxan-sodium ), prynachlor, pydanon, pymetrozine, pyracarbolid, pyraclofos, pyraclonil, pyrazole ether pyraclostrobin, pyraflufen, pyraflufen-ethyl, pyrafluprole, pyramat, pyramethstrobin, pyraoxystrobin ), pyrasulfotole, pyrazolate, pyrazophos, pyrazosulfuron-ethyl, pyrazosulfuron-ethyl, pyrazothion, benzacazole (pyrazoxyfen), anti-pyrethrum (pyresmethrin), pyrethrin I (pyrethrin I), pyrethrin II (pyrethrin II), pyrethrins (pyrethrins), pyribambenz-isopropyl ester, pyribambenz-propyl ester, pyribencarb ( pyribencarb), pyribenzoxim, pyributicarb, pyriclor, pyridaben, pyridafol, pyridalyl, pyridaphenthion, Pyridate, pyridinitril, pyrifenox, pyrifluquinazon, pyriftalid, pyrimethanil, pyrimidifen, pyriminobac ), pyriminobac-methyl, pyrimisulfan, pyrimitate, pyrinuron, pyriofenone, pyriprole, pyripropanol, Pyril Pyriproxyfen, Pyrithiobac, Pyrithiobac-sodium, Pyrolan, Pyroquilon, Pyroxasulfone, Pyroxsulam, Pyroxychlor, pyroxyfur, quassia, quinacetol, quinacetol sulfate, quinalphos, quinalphos-methyl -methyl), quinazamid, quinclorac, quinconazole, quinmerac, quinoclamine, quinonamid, Quinothion, quinoxyfen, quintiofos, quintozene, quizalofop, quizalofop-ethyl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Quwenzhi, Quyingding, Rabenzazole, rafoxanide, rebemide, resmethrin, rhodethanil, rhodojaponin-III, ribavirin ( ribavirin), rimsulfuron, rotenone, ryania, saflufenacil, saijunmao, saisentong, salicylanilide, blood Sanguinarine, santonin, schradan, scilliroside, sebutylazine, secbumeton, sedaxane, Selamectin, semiamitraz, semiamitraz chloride, sesamex, sesamoline samolin), sethoxydim, shuangjiaancaolin, siduron, siglure, silafluofen, silatrane, silica gel, silthiocarb ( silthiofam), simazine, simeconazole, simeton, simetryn, sintofen, SMA, S-metolachlor ), sodium arsenite, sodium azide, sodium chlorate, sodium fluoride, sodium fluoroacetate, sodium hexafluorosilicate, sodium naphthenate, sodium orthophenylphenoxide, five Sodium pentachlorophenoxide, sodium polysulfide, sodium thiocyanate, sodium α-naphthalene acetate, sophamide, spinetoram, spinosad, snail Spirodiclofen, spiromesifen, spirotetramat, spiroxamine, streptomycin, streptomycinsesquisulfate, streptomycin strychnine, sulcatol, sulcofuron, sulcofuron-sodium, sulcotrione, sulfallate, formazan Sulfentrazone, sulfiram, sulfluramid, sulfometuron, sulfometuron-methyl, sulfosulfuron , sulfotep, sulfoxaflor, sulfoxide, sulfoxime, sulfur, sulfuric acid, sulfuryl fluoride, sulglycapin, sulprofos, sultropen, Swep, tau-fluvalinate, tavron, tazimcarb, TCA, TCA-ammonium ), trichloroacetic acid-calcium (TCA-calci um), TCA-ethadyl, TCA-magnesium, TCA-sodium, TDE, tebuconazole, tebufenozide, Tebufenpyrad, Tebufloquin, Tebupirimfos, Tebutam, Tebuthiuron, Tecloftalam, Tecnazene , tecoram, teflubenzuron, tefluthrin, tefuryltrione, tembotrione, temephos, tepa, TEPP, tepraloxydim , terallethrin, terbacil, terbucarb, terbuchlor, terbufos, terbumeton, terbuchlor Terbutylazine, terbutryn, tetcyclacis, tetrachloroethane, tetrachlorvinphos, tetraconazole, tetradifon ), tetrafluron, tetramethrin, tetramethylfluthrin, tetramethylamine, tetranactin, tetrasul, thallium sulfate, Thienylchlor, theta-cypermethrin, thiabendazole, thiacloprid, thiadifluor, thiamethoxam, thiapronil ( thiapronil, thiazafluron, thiazopyr, thicrofos, thicyofen, thiazimin, thiazuron, thiencarbazone, thiencarbazone- Methyl esters, thifensulfuron, thiophene Thifensulfuron-methyl, thifluzamide, thiobencarb, thiocarboxime, thiochlorfenphim, thiocyclam, thiocyclam hydrochloride Salt (thiocyclam hydrochloride), thiocyclam oxalate, copper thiadiazole, thiodicarb, thiofanox, thiofluoximate, thiohempa, thiomersal , thiometon, thionazin, thiophanate, thiophanate-methyl, thioquinox, thiosemicarbazide, thiosultap , thiosultap-diammonium, thiosultap-disodium, thiosultap-monosodium, thiotepa, thiram, thuringiensin, tiadinil ), Tiaojiean, tiocarbazil, tioclorim, tioxymid, tirpate, tolclofos-methyl, tolfenpyrad, toluene fluoride Sulfa (tolylfluanid), tolylmercury acetate, topramezone, tralkoxydim, deltacythrin, tralomethrin, tralopyril, transfluthrin, transfluthrin Permethrin, tretamine, triacontanol, triadimefon, triadimenol, triafamone, tri-allate, carbafos ( triamiphos), triapenthenol, triarathene, triarimol, triasulfuron, triazamate, butyltriazole (triazbutil), triaziflam, triazophos, imidazosin (triazoxide), tribenuron, tribenuron-methyl, defoliate ( tribufos), tributyltin oxide, tricamba, trichlamide, trichlorfon, trichlormetaphos-3, trichloronat ), triclopyr, triclopyr-butoxyethyl ester (triclopyr-butotyl), triclopyr-ethyl (triclopyr-ethyl), triclopyr-triethylammonium (triclopyr-triethylammonium), three Tricyclazole, tridemorph, tridiphane, trietazine, trifenmorph, trifenofos, trifloxystrobin, Trifluxysulfuron (trifluxysulfuron), trifluxysulfuron-sodium (trifluxysulfuron-sodium), triflumizole (triflumizole), triflumuron (triflurumuron), trifluralin (trifluralin), trifluxysulfuron demethylation triflusulfuron, triflusulfuron-methyl, trifluorophenoxypropionic acid (trifop), trifluorophenoxypropionic acid-methyl (trifop-methyl), trifluoxime (trifopsime), oxazine Triforine, trihydroxytriazine, trimedlure, trimethacarb, trimeturon, trinexapac, trinexapac-ethyl, olefin Triprene, tripropindan, triptolide, tritac, triticonazole, tritosulfuron, trunc-call, alkenes Uniconazole, uniconazole-P, urbacide, uredepa, fenvalerate (v alerate), validamycin, valifenalate, valone, vamidothion, vangard, vaniliprole, vernolate, ethylene Vinclozolin, warfarin, warfarin-potassium, warfarin-sodium, xiaochongliulin, xinjunan, Xiwojunan, XMC, xylachlor, xylenols, xylylcarb, yishijing, zarilamid , zeatin, zengxiaoan, zeta-cypermethrin, zinc naphthenate, zinc phosphide, zinc thiazole, zineb, Ziram, zolaprofos, zoxamide, zuomihuanglong, alpha-chlorohydrin, alpha-ecdysone, alpha-multistriatin, and alpha - Naphthaleneacetic acid. For more information see "Compendium of Pesticide Common Names" at http://www.alanwood.net/pesticides/index.html. See also "The Pesticide Manual" 14th Edition, edited by CDS Tomlin, copyright 2006 by British Crop Production Council or previous or later editions thereof.

Biopesticide

Molecules of Formula 1 may also be used in combination (such as in a combined mixture or applied simultaneously or sequentially) with one or more biopesticides. The term "biopesticide" is used for microbial biological pest control agents that are applied in a manner similar to chemical pesticides. Typically these are bacterial control agents, but there are examples of fungal control agents including Trichoderma spp. and Ampelomyces quisqualis (for grape powdery mildew control agents). Bacillus subtilis is used to control plant pathogens. Weeds and rodents have also been controlled with microbial agents. A well known example of an insecticide is Bacillus thuringiensis, a bacterial disease of the orders Lepidoptera, Coleoptera and Diptera. Since it has little effect on other organisms, it is considered to be more environmentally friendly than synthetic insecticides. Biopesticides include products according to:

1. Entomopathogenic fungi (such as Metarhizium anisopliae);

2. Entomopathogenic nematodes (eg Steinernema feltiae); and

3. Entomopathogenic viruses (eg Cydia pomonella granulovirus).

Other examples of entomopathogens include, but are not limited to, baculoviruses, bacteria and other prokaryotes, fungi, protozoa, and Microsproridia. Biologically derived insecticides include, but are not limited to, ketones, veratridine, and microbial toxins; insect-tolerant or resistant plant species; and organisms modified by recombinant DNA techniques, thereby producing insecticides or genetically modifying An organism that conveys insect tolerance properties. Molecules of Formula 1 can be used with one or more biopesticides in the area of seed treatment and soil improvement. The Manual of Biocontrol Agents gives an overview of available biopesticide (and other biologically based control) products. Copping L.G. (ed.) (2004). The Manual of Biocontrol Agents (formerly the Biopesticide Manual) 3rd Edition. British Crop Product ion Council (BCPC), Farnham, Surrey UK.

other active compounds

Molecules of Formula 1 may also be used in combination (such as in a combination mixture or administered simultaneously or sequentially) with one or more of the following:

1.3-(4-Chloro-2,6-dimethylphenyl)-4-hydroxy-8-oxa-1-azaspiro[4,5]dec-3-en-2-one;

2.3-(4'-chloro-2,4-dimethyl[1,1'-biphenyl]-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4,5]decane -3-en-2-one;

3.4-[[(6-chloro-3-pyridyl)methyl]methylamino]-2(5H)-furanone;

4.4-[[(6-Chloro-3-pyridyl)methyl]cyclopropylamino]-2(5H)-furanone;

5.3-Chloro-N2-[(1S)-1-methyl-2-(methylsulfonyl)ethyl]-N1-[2-methyl-4-[1,2,2,2-tetrafluoro- 1-(trifluoromethyl)ethyl]phenyl]-1,2-phthalamide;

6.2-cyano-N-ethyl-4-fluoro-3-methoxy-benzenesulfonamide;

7.2-cyano-N-ethyl-3-methoxy-benzenesulfonamide;

8. 2-cyano-3-difluoromethoxy-N-ethyl-4-fluoro-benzenesulfonamide;

9. 2-cyano-3-fluoromethoxy-N-ethyl-benzenesulfonamide;

10. 2-cyano-6-fluoro-3-methoxy-N,N-dimethyl-benzenesulfonamide;

11.2-cyano-N-ethyl-6-fluoro-3-methoxy-N-methyl-benzenesulfonamide;

12.2-cyano-3-difluoromethoxy-N,N-dimethylbenzenesulfonamide;

13. 3-(Difluoromethyl)-N-[2-(3,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazole-4-carboxamide;

14. N-ethyl-2,2-dimethylpropionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone;

15. N-ethyl-2,2-dichloro-1-methylcyclopropane-carboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone nicotine (N-ethyl-2,2-dichloro-1-methylcyclopropane-carboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone nicotine);

16. O-{(E-)-[2-(4-chloro-phenyl)-2-cyano-1-(2-trifluoromethylphenyl)-vinyl]}S-methylthio Carbonate;

17. (E)-N1-[(2-Chloro-1,3-thiazol-5-ylmethyl)]-N2-cyano-N1-methylacetamidine;

18. 1-(6-Chloropyridin-3-ylmethyl)-7-methyl-8-nitro-1,2,3,5,6,7-hexahydro-imidazo[1,2-a]pyridine -5-ol;

19. 4-[4-chlorophenyl-(2-butylene-hydrazono)methyl)]phenyl methanesulfonate (4-[4-chlorophenyl-(2-butylidine-hydrazono)methyl)]phenyl mesylate); and

20. N-Ethyl-2,2-dichloro-1-methylcyclopropanecarboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone.

synergistic mixture

Molecules of Formula 1 can be used with certain active compounds whose mode of action is the same, similar or different than that of the molecule of Formula 1 to form synergistic mixtures. Examples of modes of action include, but are not limited to: acetylcholinesterase inhibitors; sodium channel modulators; chitin biosynthesis inhibitors; GABA and glutamate-gated chloride channel antagonists; chloride channel antagonist); GABA and glutamate-gated chloride channel agonist (GABA and glutamate-gated chloride channel agonist); acetylcholine receptor agonist; acetylcholine receptor antagonist; MET I inhibitor; Mg-stimulated ATPase inhibitor ( Mg-stimulated ATPase inhibitor); nicotinic acetylcholine receptors; midgut membrane disruptors; oxidative phosphorylation disruptors and brain ryanodine receptors (RyRs). Typically, the weight ratio of the molecule of Formula 1 to another compound in the synergistic mixture is from about 10:1 to about 1:10, in another embodiment from about 5:1 to about 1:5, and in another In one embodiment it is about 3:1, and in another embodiment it is about 1:1.

preparation

Insecticides are hardly suitable for application in their pure form. It is often necessary to add other substances so that the pesticide can be used in the desired concentration and in a suitable form for ease of application, handling, transport, storage and to maximize pesticide activity. Thus, insecticides are formulated, for example, as baits, concentrated emulsions, dusts, emulsifiable concentrates, fumigants, gels, granules, microencapsulations, seed treatments ( seed treatment), suspension concentrates, suspoemulsions, tablets, water soluble liquids, water dispersible granules or dry flowables, wettable powders and ultra-low volume solutions (ultraLowvolume solution). For further information on formulation types see "Catalogue of Pesticide Formulation Types and International Coding System" Technical Monograph n°2,5th Edition by CropLife International (2002).

Pesticides are most commonly applied in the form of aqueous suspensions or emulsions prepared from concentrated formulations of the insecticide. Such water-soluble, water-suspendable or emulsifiable formulations are solids (often known as wettable powders or water-dispersible granules) or liquids (often known as emulsifiable concentrates or aqueous suspensions). Wettable powders (which can be compressed to form water-dispersible granules) comprise an intimate mixture of insecticide, carrier and surfactant. The concentration of the pesticide is generally from about 10% by weight to about 90% by weight. The carrier is usually selected from attapulgite clay, montmorillonite clay, diatomaceous earth or purified silicate. Effective surfactants (from about 0.5% to about 10% of the wettable powder) are selected from sulfonated lignin, concentrated naphthalene sulfonates, naphthalene sulfonates, alkylbenzene sulfonates, alkyl sulfates Salts and nonionic surfactants (such as ethylene oxide adducts of alkylphenols).

Emulsifiable concentrates of insecticides comprise an insecticide at a suitable concentration (e.g., from about 50 to about 500 grams per liter of liquid) dissolved in a carrier which is a water-miscible solvent or a mixture of a water-immiscible organic solvent and an emulsifier . Useful organic solvents include aromatic solvents (especially xylenes) and petroleum fractions (especially the high boiling naphthalene and olefinic portions of petroleum such as heavy aromatic naphtha). Other organic solvents such as terpenoid solvents (including rosin derivatives), aliphatic ketones such as cyclohexanone, and complex alcohols such as 2-ethoxyethanol may also be used. Suitable emulsifiers for emulsifiable concentrates are selected from common anionic and nonionic surfactants.

Aqueous suspensions include suspensions of water-insoluble pesticides dispersed in an aqueous carrier at a concentration of about 5% to about 50% by weight. Suspensions are prepared by finely grinding the insecticide and vigorously mixing it into a vehicle comprising water and surfactants. Ingredients such as inorganic salts and synthetic or natural gums may also be added to increase the density and viscosity of the aqueous carrier. It is often most effective to simultaneously grind and mix the insecticide by preparing and homogenizing an aqueous mixture in equipment such as a sand mill, ball mill, or piston-type homogenizer agent.

Pesticides may also be applied in the form of granular compositions which are particularly useful for application to soil. Granular compositions generally contain from about 0.5% to about 10% by weight of the insecticide dispersed in a carrier comprising clay or similar material. Such compositions are generally prepared by dissolving the insecticide in a suitable solvent and applying it to a granular carrier which has been preformed to a suitable particle size (in the range of about 0.5 to 3 mm). The compositions described above may also be prepared by forming the carrier and compound into a dough or paste, which is then crushed and dried to obtain the desired particle size.

Dusts containing insecticides are prepared by thoroughly mixing powdered insecticides with a suitable dusty agricultural carrier (eg kaolin clay, ground volcanic rock, etc.). Dusts may suitably contain from about 1% to about 10% insecticide. They can be used for seed dressing or with dust blowers for foliage application.

It is also possible to apply the insecticides in solution (in suitable organic solvents (usually petroleum oils such as spray oils) widely used in agrochemicals).

Pesticides may also be applied in the form of aerosol compositions. In such compositions, the insecticide is dissolved or dispersed in a carrier, which is a pressure-generating propellant mixture. The aerosol composition is packaged in a container and the mixture is dispensed from the container through an atomizing valve.

Insecticide baits are formed when an insecticide is mixed with food or attractant or with food and attractant. When pests eat the bait, they also consume the insecticide. Baits can be in the form of granules, gels, flowable powders, liquids or solids. They are used in pest hideouts.

Fumigants are insecticides that have a relatively high vapor pressure and therefore can be present in gaseous form, which kills pests in soil or enclosed spaces in sufficient concentrations. The toxicity of a fumigant is proportional to its concentration and exposure time. They are characterized by a good dispersal capacity and act by penetrating into the respiratory system of the pest or being absorbed through the cuticle of the pest. Fumigants are applied for the control of stored product pests under gas proof sheets in airtight rooms or buildings or in specialized chambers.

Pesticides can be microencapsulated by suspending particles or droplets of the pesticide in various types of plastic polymers. Microcapsules of various sizes, various solubilities, various wall thicknesses, and various degrees of permeability can be formed by changing the chemical nature of the polymer or by changing factors in the processing. These factors control the release rate of the active ingredient in it, which in turn affects the residual properties, speed of action and odor of the product.

Oil solution concentrates are prepared by dissolving the insecticide in a solvent that keeps the insecticide in solution. Oil solutions of insecticides generally provide faster knockdown and kill than other formulations due to the insecticidal action of the solvent itself and the dissolution of the waxy covering of the integument which increases the rate of insecticide uptake. Kill pests. Other advantages of oil solutions include better storage stability, better crack penetration and better adhesion to greasy surfaces.

Another embodiment is an oil-in-water emulsion, wherein said emulsion comprises oily globules each provided with a lamellar liquid crystal coating and dispersed in an aqueous phase, wherein each The oily globules contain at least one agriculturally active compound and are each coated with a single layer or several layers comprising (1) at least one nonionic lipophilic surfactant, (2) at least one nonionic hydrophilic surfactant and (3) at least one ionic surfactant, wherein the globules have an average particle size of less than 800 nanometers. Further information on this embodiment is disclosed in US Patent Publication 20070027034 (published February 1, 2007 and patent application Ser. No. 11/495,228). For ease of use, this embodiment is referred to as "OIWE".

For further information see "Insect Pest Management" 2nd Edition by D. Dent, copyright CAB International (2000). Also, for more details see "Handbook of Pest Control-The Behavior, Life History, and Control of Household Pests" by Arnold Mallis, 9th Edition, copyright2004 by GIE Media Inc.

Other formulation components

Generally, when the invention disclosed herein is used in a formulation, the formulation may also contain other components. These components include, but are not limited to (this is a non-exhaustive and non-mutually exclusive list) wetting agents, spreaders, adhesives, penetrants, buffers, sequestering agents, anti-drift agent (drift reduction agent), compatibilizer (compatibility agent), defoamer, detergent and emulsifier. Several components are described next.

Wetting agents are substances which, when added to a liquid, increase the spreading or penetrating ability of the liquid by lowering the interfacial tension between the liquid and the surface on which the liquid is spreading. Wetting agents perform two main functions in agrochemical formulations: increasing the wetting rate of powders in water during handling and manufacturing to prepare concentrates or suspension concentrates in soluble liquids; Reduces wetting time of wettable powders and improves penetration of water into water dispersible granules during in-tank mixing. Examples of wetting agents used in wettable powder, suspension concentrate and water dispersible granule formulations are sodium lauryl sulfate, sodium dioctylsulphosuccinate, alkylphenol ethoxylates and fatty alcohol ethoxylates.

Dispersants are substances that adsorb to the surface of particles and help maintain the particles in a dispersed state and prevent the particles from re-agglomerating. Dispersants are added to agrochemical formulations to aid in dispersion and suspension during manufacture and to help ensure redispersion of particles into water in spray tanks. They are widely used in wettable powders, suspension concentrates and water dispersible granules. Surfactants used as dispersants have the ability to adsorb strongly onto particle surfaces and provide a charged or steric barrier against particle reagglomeration. The most commonly used surfactants are anionic surfactants, nonionic surfactants or a mixture of these two types. For wettable powder formulations, the most common dispersant is sodium lignosulphonate. For suspension concentrates, very good adsorption and stabilization are obtained using polyelectrolytes such as sodium naphthalene sulphonate formaldehyde condensate. Tristyrylphenol ethoxylate phosphate esters are also used. Nonionic surfactants such as alkylarylethylene oxide condensates and EO-PO block copolymers are sometimes combined with anionic surfactants as dispersants for suspension concentrates. In recent years, new classes of very high molecular weight polymeric surfactants have been developed as dispersants. These dispersants have a very long hydrophobic "backbone" and many ethylene oxide chains forming the "teeth" of a "comb" like surfactant. These high molecular weight polymers provide very good long-term stability for suspension concentrates due to the hydrophobic backbone having multiple anchor points fixed to the particle surface. Examples of dispersants used in agrochemical formulations are sodium lignosulfonate, sodium naphthalenesulfonate formaldehyde condensate, tristyrylphenol ethoxylate phosphate ester, fatty alcohol ethoxylate, alkyl ethoxylate compounds, EO-PO block copolymers and graft copolymers.

An emulsifier is a substance that stabilizes a suspension of droplets of one liquid phase in another liquid phase. In the absence of an emulsifier, the two liquids would separate into two immiscible liquid phases. The most commonly used emulsifier blends contain an alkylphenol or fatty alcohol with 12 or more ethylene oxide units and an oil-soluble calcium salt of dodecylbenzenesulfonic acid. A Hydrophile-Lipophile Balance ("HLB") value in the range of 8 to 18 will generally provide a good stable emulsion. Emulsion stability can sometimes be improved by adding a small amount of EO-PO block copolymer surfactant.

Solubilizers are surfactants that form micelles in water at concentrations above the critical micelle concentration. The micelles are then able to dissolve or solubilize water-insoluble substances within the hydrophobic portion of the micelles. The types of surfactants commonly used for solubilization are nonionic: sorbitan monooleate, sorbitan monooleate ethoxylate, and oleic acid Methyl oleate ester.

Surfactants are sometimes used alone or in combination with other additives, such as mineral or vegetable oils as adjuncts to spray tank mixtures, to improve the biological performance of the insecticide on the target. The type of surfactant used for bioenhancement generally depends on the nature and mode of action of the insecticide. However, they are usually non-ionic, such as alkyl ethoxylates, linear fatty alcohol ethoxylates, fatty amine ethoxylates.

A carrier or diluent in an agricultural formulation is a substance added to a pesticide to give a product of the desired strength. Carriers are generally substances with high absorptive capacity, while diluents are generally substances with low absorptive capacity. Carriers and diluents are used in powder formulations, wettable powder formulations, granule formulations and water-dispersible granule formulations.

Organic solvents are mainly used in emulsifiable concentrate formulations, oil-in-water emulsions, suspoemulsions and ULV formulations and to a lesser extent in granular formulations. Sometimes mixtures of solvents are used. Solvents of the first main group are aliphatic paraffinic oils such as kerosene or refined paraffin. The second major group and most common solvents include aromatic solvents such as xylenes and the higher molecular weight fractions ie _C9 and _C10 aromatic solvents. Chlorinated hydrocarbons can be used as co-solvents to prevent crystallization of the pesticide when emulsifying the formulation into water. Alcohols are sometimes used as co-solvents to increase solvent power. Other solvents may include vegetable oils, seed oils, and esters of vegetable and seed oils.

Thickeners or gelling agents are mainly used in suspension concentrate formulations, emulsion formulations and suspoemulsion formulations to modify the rheology or fluidity of liquids and to prevent separation or settling of dispersed particles or droplets. Thickeners, gelling agents and anti-settling agents are generally divided into two categories, namely water-insoluble particles and water-soluble polymers. It is possible to produce suspension concentrate formulations using clays and silicas. Examples of these types of materials include, but are not limited to, montmorillonites, such as bentonite; magnesium aluminum silicate; and attapulgite. Water-soluble polysaccharides have been used as thickening-gelling agents for many years. The most commonly used types of polysaccharides are natural extracts from seeds or seaweeds or synthetic derivatives of cellulose. Examples of these types of substances include, but are not limited to, guar gum, locust beangum, carrageenam, alginate, methylcellulose, sodium carboxymethylcellulose (SCMC), hydroxyethyl cellulose base cellulose (HEC). Other types of anti-settling agents are based on modified starches, polyacrylates, polyvinyl alcohols and polyethylene oxides. Another good anti-settling agent is xanthan gum.

Microorganisms cause spoilage of formulated products. Preservatives are therefore used to eliminate or reduce the action of microorganisms. Examples of these agents include, but are not limited to, propionic acid and its sodium salt, sorbic acid and its sodium or potassium salt, benzoic acid and its sodium salt, sodium paraben, methyl paraben, and 1,2-benzene isothiazolin-3-one (BIT).

The presence of interfacial tension-lowering surfactants often results in foaming of water-based formulations during mixing operations when produced and applied via spray tanks. In order to reduce the foaming tendency, antifoaming agents are usually added during the production stage or before filling into the bottle. In general, there are two types of defoamers namely silicone and non-silicone. Silicones are usually aqueous emulsions of dimethicone, while non-silicone antifoams are water insoluble oils such as octanol and nonanol. In both cases, the function of the defoamer is to displace the surfactant from the air-water interface.

"Green" agents (eg excipients, surfactants, solvents) can reduce the overall environmental footprint of crop protection formulations. Green agents are biodegradable and are typically derived from natural and/or available sources such as plant and animal sources. Particular examples are: vegetable oils, seed oils and esters of vegetable and seed oils, and alkoxylated alkyl polyglucosides.

For further information see "Chemistry and Technology of Agrochemical Formulations" edited by D.A. Knowles, copyright 1998 by Kluwer Academic Publishers. See also "Insecticides in Agriculture and Environment-Retrospects and Prospects" by A.S. Perry, I. Yamamoto, I. Ishaaya, and R. Perry, copyright 1998 by Springer-Verlag.

pest

In general, the molecules of Formula 1 are useful for controlling pests such as beetles, earwigs, cockroaches, flies, aphids, scales, whiteflies , leafhopper, ant, wasp, termite, moth, butterfly, lice, grasshopper, locust, cricket ), fleas, thrips, bristletails, mites, ticks, nematodes and Symphyla.

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the Phyla Nematoda and/or Arthropoda.

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the Subphyla Chelicerata, Myriapoda and/or Hexapoda.

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the classes Arachnida, Symphyla and/or Insecta.

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the Order Anoplura. A non-exhaustive list of specific species includes, but is not limited to, Haematopinus spp., Hoplopleura spp., Linognathus spp., Pediculus spp. and Scale lice (Polyplax spp.). A non-exhaustive list of specific species includes, but is not limited to, donkey blood lice (Haematopinus asini), pig blood lice (Haematopinus suis), hair lice (Linognathus setosus), sheep jaw lice (Linognathus ovillus), head lice (Pediculus humanus capitis), Body lice (Pediculus humanus humanus) and pubic lice (Pthirus pubis).

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Coleoptera. A non-exhaustive list of specific species includes, but is not limited to, Acanthoscelides spp., Agriotes spp., Anthonomus spp., Apions pp. , Apogonia spp., Aulacophora spp., Bruchus spp., Cerosterna spp., Cerotoma spp., Ceutorhynchus spp.), Chaetocnema spp., Colaspis spp., Cteniceraspp., Curculio spp., Cyclocephala spp., Diabrotica spp .), Hypera spp., Ips spp., Lyctus spp., Megascelis spp., Meligethes spp., Otiorhynchus spp. ), Pantomorus spp., Phyllophaga spp., Phyllotreta spp., Rhizotrogus spp., Rhynchitesspp ., Rhynchophorus spp., Scolytus spp., Sphenophorus spp., Sitophilus spp. and Tribolium spp. A non-exhaustive list of specific species includes, but is not limited to, the common bean weevil (Acanthoscelides obtectus), the white wax narrow beetle (Agrilus planipennis), the bald beetle (Anoplophora glabripennis), the cotton boll weevil (Anthonomus grandis), the black velvet beetle (Ataenius spretulus), Atomaria linearis, Beet elephant (Bothynoderes punctivecentris), Pea elephant (Bruchus pisorum), Callosobruchus maculatus (Callosobruchus maculatus), Macular beetle (Carpophilus hemipterus), Beet tortoise (Cassida vittata), Cerotoma trifurcata, Cabbage tortoise (Ceutorhynchus assimilis), Ceutorhynchus napi, Conoderus scalaris, Conoderus stigmosus, Conotrachelus nenuphar, Cotinis nitida, Crioceris asparagi, Cryptolestes ferrugineus , Cryptolestes pusillus, Cryptolestes turcicus, Cylindrocopturus adspersus, Deporaus marginatus, Dermestes lardarius, Dermestesmaculatus, Mexican beetle Ladybug (Epilachna varivestis), Stem borer weevil (Faustinus cubae), Pale root neck weevil (Hylobius pales), Clover leaf weevil (Hypera postica), Coffee berry beetle (Hypothenemus hampei), Tobacco beetle (Lasioderma serricorne), Potato beetle (Leptinotarsa decemlineata), Liogenys fuscus, Liogenys suturalis, Rice water weevil (Lissorhoptrus oryzophilus), Maecolaspis joliveti, Corn beetle (Melanotuscommunis), Rapeseed weevil (Meligethe s aeneus), May beetle (Melolonthamelolontha), Oberea brevis, linear beetle (Oberea Linearis), coconut borer beetle (Oryctesrhinoceros), trade saw beetle (Oryzaephilus mercator), saw beetle (Oryzaephilussurinamensis), black horned beetle Oulema melanopus, Oulema oryzae, Phyllophaga cuyabana, Popillia japonica, Prostephanustruncatus, Rhyzopertha dominica, Sitona lineatus, Grain elephant (Sitophilus granarius), Rice elephant (Sitophilus oryzae), Corn elephant (Sitophilus zeamais), Medicinal beetle (Stegobium panicum), Red corn beetle (Tribolium castaneum), Miscellaneous grain beetle (Tribolium confusum), Versicolor beetle (Trogoderma variabile) and Zabrus tenebrioides.

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Dermaptera.

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Blattaria. A non-exhaustive list of specific species includes, but is not limited to, Blattella germanica, Blatta orientalis, Parcoblatta pennsylvanica, Periplaneta americana, Periplaneta australasiae ), brown cockroach (Periplaneta brunnea), smoked cockroach (Periplaneta fuliginosa), green cockroach (Pycnoscelus surinamensis) and long bearded cockroach (Supella longipalpa).

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Diptera. A non-exhaustive list of specific species includes, but is not limited to, Aedes spp., Agromyza spp., Anastrepha spp., Anopheles spp. .), Bactrocera spp., Ceratitis spp., Chrysops spp., Cochliomyia spp., Gall midges ( Contarinia spp.), Culex spp., Dasineura spp., Delia spp., Drosophila spp., Drosophila spp. Species (Fannia spp.), Hylemyia spp., Liriomyza spp., Musca spp., Phorbia spp., Tabanus spp. and Tipula spp. A non-exhaustive list of specific species includes, but is not limited to, Agromyza frontella, Anastrepha suspensa, Anastrepha ludens, Anastrepha obliqa, melon Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocerainvadens, Bactrocera zonata, Ceratitis capitata, Dasineura brassicae, Delia platura, Fannia canicularis, Fannia scalaris, Gasterophilus intestinalis, Gracillia perseae, Haematobia irritans, Hypoderma lineatum ), Liriomyza brassicae, Melophagus ovinus, Musca autumnalis, Musca domestica, Oestrus ovis, Oscinella frit, sugar beet Spring fly (Pegomya betae), carrot stalk fly (Psila rosae), cherry fruit fly (Rhagoletis cerasi), apple fruit fly (Rhagoletis pomonella), blue fruit fly (Rhagoletismendax), wheat red midge (Sitodiplosis mosellana) and stable sting fly (Stomoxys calcitrans),

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Hemiptera. A non-exhaustive list of specific species includes, but is not limited to, Adelges spp., Aulacaspis spp., Aphrophora spp., Aphis spp. .), Bemisia spp., Ceroplastes spp., Chionaspisspp., Chrysomphalus spp., Soft wax scale ( Coccus spp.), Empoasca spp., Lepidosaphes spp., Lagynotomus spp., Lygus spp., Lygus spp. Macrosiphum spp., Nephotettix spp., Nezara spp., Philaenus spp., Phytocoris spp. , Piezodorus spp., Planococcus spp., Pseudococcus spp., Rhopalosiphum spp., Saissetias pp., Therioaphis spp. ), Toumeyella spp., Toxopteras pp., Trialeurodes spp., Triatoma spp. and Unaspis spp. A non-exhaustive list of specific species includes, but is not limited to, Acrosternum hilare, Acyrthosiphon pisum, Aleyrodes proletella, Aleurodicus dispersus, Aleurothrixus floccosus, Amrasca biguttula biguttula, Red round scale (Aonidiella aurantii), cotton aphid (Aphis gossypii), soybean aphid (Aphis glycines), apple aphid (Aphis pomi), potato bearded aphid (Aulacorthum solani), silver leaf whitefly (Bemisia argentifolii), sweet potato whitefly ( Bemisia tabaci), Blissus leucopterus, Brachycorynella asparagi, Brevennia rehi, Brevicorynebrassicae, Calocoris norvegicus, Ceroplastes rubens, Tropical bed bug (Cimex hemipterus), Temperate bedbug (Cimex lectularius), Dagbertus fasciatus, Dichelops furcatus, Diuraphis noxia, Diaphorinacitri, Dysaphis plantaginea, Dysdercus suturellus), Edessa meditabunda, Eriosoma lanigerum, Eurygastermaura, Euschistus heroos, Euschistus servus, Helopeltis antonii, Helopeltis theivora , Icerya purchasi, Idioscopus nitidulus, Laodelphax striatellus, Leptocorisaoratorius, Leptocorisa varicornis, Lygus hesperus), hibiscus mealybug (Maconellicoccu hirsutus), Macrosiphum euphorbiae, Macrosiphum granarium, Macrosiphum rosae, Macrosteles quadrilineatus, Mahanarva frimbiolata, Metopolophium dirhodum, Mictis longicornis, peach Aphids (Myzus persicae), black-tailed leafhoppers (Nephotettixcinctipes), Neurocolpus longirostris, green bugs (Nezara viridula), brown planthoppers (Nilaparvata lugens), parlatoria pergandii, parlatoriaziziphi, popcorn flowers Winged Planthopper (Peregrinus maidis), Grape Phylloxera (Phylloxera vitifoliae), Physokermes piceae, Phytocoris californicus, Phytocoris relativus, Piezodorus guildinii, Poecilocapsus lineatus, Psallus vaccinicola, Pseudacysta perseae, pineapple Pseudococcus brevipes, Quadraspidiotus perniciosus, Rhopalosiphum maidis, Rhopalosiphum padi, Saissetia oleae, Scaptocoris castanea, Aphid aphid (Schizaphis graminum), wheat long tube aphid (Sitobion avenae), white-backed planthopper (Sogatella furcifera), greenhouse whitefly (Trialeurodes vaporariorum), knot-winged whitefly (Trialeurodes sabutiloneus), arrow-tip scale (Unaspis yanonensis) and Zulia entrerriana.

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Hymenoptera. A non-exhaustive list of specific species includes, but is not limited to, Acromyrmex spp., Atta spp., Camponotus spp., Diprion spp. spp.), Formica spp., Monomorium spp., Neodiprion spp., Pogonomyrmex spp., Polistes spp.), Solenopsis spp., Vespula spp. and Xylocopaspp. A non-exhaustive list of specific species includes, but is not limited to, Athalia rosae, Attatexana, Iridomyrmex humilis, Monomorium minimum, Monomorium pharaonis, Solenopsis invicta ), tropical fire ants (Solenopsis geminata), Solenopsis molesta, black fire ants (Solenopsis richtery), southern fire ants (Solenopsis xyloni) and stink house ants (Tapinoma sessile).

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Isoptera. A non-exhaustive list of specific species includes, but is not limited to, Coptotermes spp., Cornitermes spp., Cryptotermes spp., Heterotermes spp. ), Kalotermes spp., Incisitermesspp., Macrotermes spp., Marginitermes spp., Microcerotermes spp. ), Procornitermes spp., Reticulitermes spp., Schedorhinotermes spp. and Zootermopsis spp. A non-exhaustive list of specific species includes, but is not limited to, Coptotermes curvignathus, Coptotermes frenchii, Coptotermes formosanus, Heterotermes aureus, Microtermes obesi), Reticulitermes banyulensis, Reticulitermes grassei, Reticulitermes flavipes, Reticulitermes hageni, Reticulitermes hesperus, Reticulitermes santonensis, Reticulitermes santonensis ( Reticulitermes speratus), Reticulitermes tibialis and Reticulitermes virginicus.

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Lepidoptera. A non-exhaustive list of specific species includes, but is not limited to, Adoxophyes spp., Agrotis spp., Argyrotaenia spp., Cacoecia spp., Caloptilias spp. , Chilo spp., Chrysodeixis spp., Colias spp., Crambus spp., Diaphania spp. .), Diatraea spp., Earias spp., Ephestia spp., Epimecisspp., Feltia spp., Gortyna spp. , Helicoverpa spp., Heliothis spp., Indarbela spp., Lithocolletis spp., Loxagrotis spp., Malacosoma spp., Peridroma spp. Phyllonorycterspp., Pseudaletia spp., Sesamia spp., Spodopteraspp., Synanthedon spp. Yponomeuta spp.). A non-exhaustive list of specific species includes, but is not limited to, Achaea janata, Adoxophyes orana, Agrotis ipsilon, Alabama argillacea, Amorbia cuneana . Argyrotaenia citrana, Autographagamma, Bonagota cranaodes, Borbo cinnara, Bucculatrix thurberiella, Capua reticulana, Carposina niponensis, Mangota cranaodes Chlumetia transversa, Choristoneura rosaceana, Cnaphalocrocis medinalis, Conopomorpha cramerella, Cossus cossus, Cydia caryana, Cydia funebrana , Cydia molesta, Cydia nigricana, Cydia pomonella, Darna diducta, Diatraea asaccharalis, Diatraea graniosella, Egyptian diamond (Eariasinsulata), emerald diamond (Earias vitella), Ecdytolopha aurantianum, Elasmopalpus lignosellus, Ephestia cautella, Ephestia elutella, Ephestia kuehniella, Epinotiaaporema , light brown apple moth (Epiphyas postvittana), banana butterfly (Epiphyas postvittana), rionota thrax), Eupoecilia ambiguella, Euxoa auxiliaris, Eastern fruit borer (Grapholitamolesta), three-printed borer moth (Hedylepta indicata), cotton bollworm (Helicoverpa armigera), corn beetle (Helicoverpa zea), Heliothis virescens, Hellulaundalis, Keiferia lycopersicella, Leucinodes orbonalis, Perileucoptera coffeeella, Leucoptera malifoliella), Lobesia botrana, Loxagrotis albicosta, Lymantria dispar, Lyonetia clerkella, Mahasena corbetti, Mamestra brassicae, Maruca testulalis, Bag moth (Metisa plana), Mythimna unipuncta, Neoleucinodes elegantalis, Three-spotted water borer (Nymphula depunctalis), Fall inchworm (Operophtera brumata), Corn borer (Ostrinia nubilalis), Oxydia vesulia, Pandemiscerasana, Brown apple moth (Pandemis heparana), African Dharma butterfly (Papilio demodocus), red boll moth (Pectinophora gossypiella), variegated cutworm (Peridroma saucia), coffee leafminer (Perileucoptera coffeeella), potato tuber moth (Phthorimaea operculella), citrus leafminer ( Phyllocnisitis citrella), Pieris rapae, Plathypenascabra, Plodia interpunctella, Plutella xylostella, Polychrosis viteana, Prays endocarpa, Olive moth (Pra ys oleae), Pseudaletia unipuncta, soybean armyworm (Pseudoplusia includens), inchworm (Rachiplusianu), rice stem borer (Scirpophaga incertulas), rice stem borer (Sesamia inferens), powder stem borer (Sesamia nonagrioides), copper-spotted brown thorn Moth (Setora nitens), Wheat moth (Sitotroga cerealella), Grape beard moth (Sparganothis pilleriana), Beet armyworm (Spodoptera exigua), Meadowworm (Spodoptera fugiperda), Southern gray winged moth (Spodoptera oridania), The clabasilides, clothes moth (Tineola bisselliella), mealworm (Trichoplusia ni), tomato leafminer (Tuta absoluta), coffee leopard beetle moth (Zeuzera coffeeae) and pear leopard beetle moth (Zeuzera pyrina).

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Mallophaga. A non-exhaustive list of specific species includes, but is not limited to, Anaticola spp., Bovicola spp., Chelopistes spp., Goniodes spp., Menacanthus spp., and Trichodectes spp. A non-exhaustive list of specific species includes, but is not limited to, Bovicola bovis, Bovicola caprae, sheep louse (Bovicola ovis), Chelopistes meleagridis, Goniodes dissimilis, Goniodes gigas, turkey shorthorned bird louse (Menacanthus stramineus), chicken feather louse (Menopon gallinea) and canine biting lice (Trichodectes canis).

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Orthoptera. A non-exhaustive list of specific species includes, but is not limited to, Melanoplus spp. and Pterophylla spp. A non-exhaustive list of specific species includes, but is not limited to, Anabrussimplex, Gryllotalpa africana, Gryllotalpa australis, Gryllotalpabrachyptera, mole cricket (Gryllotalpa hexadactyla), Locusta migratoria, Weta (Microcentrum retinarve), Desert Grasshopper (Schistocerca gregaria) and Fork-tailed Squidweed (Scudderia furcata).

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Siphonaptera. A non-exhaustive list of specific species includes, but is not limited to, Ceratophyllus gallinae, Ceratophyllus niger, Ctenocephalides canis, Ctenocephalides felis, and Pulex irritans.

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Thysanoptera. A non-exhaustive list of specific species includes, but is not limited to, Caliothrips spp., Frankliniella spp., Scirtothrips spp., and Thrips spp. A non-exhaustive list of specific species includes, but is not limited to, Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella williamsi, Heliothrips haemorrhaidalis, Rhipiphorothrips cruentatus, Scirtothrips citri, Scirtothrips dorsalis and Taeniothripsrhopalantennalis, Thrips hawaiiensis, Thrips nigropilosus, Thrips orientalis and Thrips tabaci .

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Thysanura. A non-exhaustive list of specific species includes, but is not limited to, Lepisma spp. and Thermobia spp.

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the order Acarina. A non-exhaustive list of specific species includes, but is not limited to, Acarus spp., Aculops spp., Boophilus spp., Demodex spp.), Dermacentor spp., Epitimerus spp., Eriophyesspp., Ixodes spp., Ixodes spp. Oligonychus spp.), Panonychus spp., Rhizoglyphus spp. and Tetranychus spp. A non-exhaustive list of specific species includes, but is not limited to, Acarapis woodi, Acarus siro, Aceria mangiferae, Aculopslycopersici, Aculus pelekassi, Aculus siro Aculus schlechtendali, Amblyomma americanum, Brevipalpus obovatus, Brevipalpusphoenicis, Dermacentor variabilis, Dermatophagoidespteronyssinus, Eotetranychus carpini ), Notoedres cati, Oligonychus coffee, Oligonychus ilicus, Panonychus citri, Panonychus ulmi, rugose leaf Phyllocoptruta oleivora, Polyphagotarsonemun latus, Rhipicephalus sanguineus, Sarcoptes scabiei, Tegolophus perseaflorae, Tegolophus perseaflorae (Tetranychus urticae) and Varroa destructor (Varroadestructor).

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the class Symphyla. A non-exhaustive list of specific species includes, but is not limited to, white pine worm (Scutigerella immaculata).

In another embodiment, the molecules of Formula 1 are useful for controlling pests of the Phylum Nematoda. A non-exhaustive list of specific species includes, but is not limited to, Aphelenchoides spp., Belonolaimus spp., Criconemella spp., Ditylenchus spp. spp.), Heteroderas pp., Hirschmanniella spp., Hoplolaimus spp., Meloidogyne spp., Brachymus spp. (Pratylenchus spp.) and Radopholus spp. A non-exhaustive list of specific species includes, but is not limited to, Dirofilaria immitis, Heterodera zeae, Meloidogyne incognita, Meloidogyne javanica, Onchocercavolvulus , Radopholus similis and Banana reniform nematode (Rotylenchus reniformis).

For more detailed information, please refer to "Handbook of Pest Control-The Behavior, Life History, and Control of Household Pests" by Arnold Mallis, 9th Edition, copyright2004 by GIE Media Inc.

apply

Molecules of Formula 1 are generally used for control in amounts ranging from about 0.01 grams per hectare to about 5000 grams per hectare. Amounts of about 0.1 grams per hectare to about 500 grams per hectare are preferred and amounts of about 1 gram per hectare to about 50 grams per hectare are generally more preferred.

The area to which the molecule of Formula 1 is applied may be any area occupied by (or may be inhabited or passed by) pests, for example: areas where crops, trees, fruits, grains, fodder, vines, grasses, and ornamental plants grow; areas inhabited by domestic animals Area; the interior or exterior surfaces of buildings (such as where grain is stored), construction materials used in buildings (such as impregnated wood), and the soil surrounding buildings. Specific crop areas using molecules of formula 1 include apple, corn, sunflower, cotton, soybean, canola, wheat, rice, sorghum, barley, oats, potatoes, oranges, alfalfa, lettuce, strawberry, tomato, pepper, cruciferous Areas where plants, pears, tobacco, almonds, sugar beets, beans and other valuable crops are growing or their seeds are about to be sown. It is also advantageous to use aluminum sulfate with molecules of formula 1 in the growth of various plants.

Pest control generally means that pest populations, pest activity, or both are reduced in an area. This may occur when: the pest population is repelled from the area; the pest becomes incapacitated in or around the area; or the pest becomes extinct in whole or in part in or around the area. Of course, combinations of these results can occur. Generally, pest population, activity, or both are expected to be reduced by more than 50%, more preferably by more than 90%. Generally, the area is not in or on the surface of humans; therefore, the location is usually a non-human area.

Molecules of formula 1 may be used in mixtures, applied simultaneously or sequentially, alone or with other compounds that enhance plant vigor (eg grow better roots, better withstand stressful growing conditions). Said other compounds are, for example, compounds which modulate plant ethylene receptors, most recently 1-methylcyclopropene (also known as 1-MCP). Moreover, the molecule could be used when pest activity is low, such as before growing plants begin to produce valuable agricultural products. This period includes the early planting season when pest pressure is usually low.

Molecules of Formula 1 can be applied to the foliage and fruit parts of plants to control pests. The molecule will come into direct contact with the pest, or the pest will consume the pesticide when it eats the foliage, fruit, or leached sap containing the pesticide. The molecules of formula 1 can also be applied to the soil and when applied in this manner, pest infestation of roots and stems can be controlled. The roots absorb molecules and draw them up to the foliage parts of the plant to control pests that chew on the ground and eat the sap.

In general, with regard to baits, the baits are placed, for example, in a location where termites can come into contact with and/or attach to the baits. Baits can also be applied to building surfaces (horizontal, vertical or inclined) where ants, termites, cockroaches and flies, for example, can come into contact with and/or cling to the bait. The bait may comprise a molecule of Formula 1.

The molecule of Formula 1 can be encapsulated inside the capsule or placed on the surface of the capsule. The size of the capsules can range from nano-sized (approximately 100-900 nanometers in diameter) to micron-sized (approximately 10-900 microns in diameter).

Due to the unique ability of the eggs of some pests to resist the action of insecticides, repeated applications of the molecule of Formula 1 may be required to control emerging larvae.

Systematic movement of a pesticide in a plant can be used to control a pest on another part of the plant by applying (eg, spraying in an area) the molecule of Formula 1 to a different part of the plant. For example, foliar-eating insects can be controlled by drip irrigation or furrow application of the soil with eg a drench before or after planting the soil, or by treating the seeds before planting.

Seed treatments can be applied to all types of seeds, including those that can grow into plants genetically transformed to express particular traits. Representative examples include those seeds that express proteins or other insecticidal toxins that are toxic to invertebrate pests (such as Bacillus thuringiensis), express herbicide resistance (such as "Roundup Ready" seeds), or have "stacking Those seeds of "exogenous genes (the"stacked"exogenous genes express insecticidal toxins, herbicide resistance, nutrient-enhancing traits, or any other beneficial traits). In addition, said seed treatment with molecules of Formula 1 may further enhance the ability of plants to better withstand stressful growing conditions. This results in healthier and more vigorous plants, which can result in higher yields at harvest. In general, good benefit is expected to be obtained from the application of about 1 gram to about 500 grams of the molecule of Formula 1 per 100,000 seeds, and better benefit is expected to be obtained from about 10 grams to about 100 grams per 100,000 seeds. And amounts of about 25 grams to about 75 grams per 100,000 seeds are expected to yield even better benefits.

It will be readily appreciated that molecules of formula 1 can be used in plants that are genetically transformed to express specific traits, such as Bacillus thuringiensis or other insecticidal toxins, or to express herbicide resistance, or to plants with "stacked" foreign genes , said "stacking" exogenous genes express insecticidal toxins, herbicide resistance, nutrient-enhancing traits, or any other beneficial trait.

Molecules of formula 1 are useful in the control of endoparasites and ectoparasites in veterinary medicine or in the field of non-human animal husbandry. The molecules of formula 1 are administered orally in the form of e.g. tablets, capsules, drinks, granules, in the form of e.g. dipped, sprayed, poured, spotted and dusted Skin administration is carried out, and parenteral administration is carried out in the form of, for example, injections.

Molecules of formula 1 may also be advantageously used in livestock farming (eg cattle, sheep, pigs, chickens and geese). They are also advantageously employed in pets such as horses, dogs and cats. Particular pests to be controlled may be fleas and ticks, which are a nuisance to the animals. Suitable formulations are administered orally to animals with drinking water or feed. Proper dosage and formulation are species dependent.

Molecules of formula 1 are also useful for controlling parasitic helminths in the animals listed above, especially intestinal helminths.

Molecules of Formula 1 may also be employed in methods of treatment for human health care. Such methods include, but are not limited to, oral administration in the form of, for example, tablets, capsules, drinks, granules, and application through the skin.

Pests all over the world are migrating to new environments (for such pests) and then becoming new invasive species in this new environment. Molecules of formula 1 can also be used on such new invading species to control them in this new environment.

Molecules of Formula 1 may also be used in areas where plants such as crops are growing (e.g., before, during, before harvest) and where the presence of low levels (or even no actual presence) of such Pests of plants. The use of this molecule in such an area is to benefit the plants growing in that area. Such benefits may include, but are not limited to, improved plant health, improved plant yield (e.g., increased biomass and/or increased content of valuable components), improved plant vigor (e.g., improved plant growth and/or more green leaves), improved plant quality (eg, improved content or composition of certain ingredients) and improved plant tolerance to abiotic and/or biotic stress.

Pesticides undergo a lengthy evaluation process by various government authorities (local, regional, state, national, international) before they can be used or sold commercially. The voluminous data requirement is specified by the regulatory authority and must be addressed by data generation and submitted by the product registrant or by others on behalf of the product registrant, usually using an Internet connection Computer. These government authorities then evaluate the data and, if a safety determination is made, provide product registration approval to potential users or sellers. Thereafter, said users or sellers may use or sell these pesticides where product registration is authorized and supported.

Molecules of Formula 1 can be tested to determine efficacy against pests. Furthermore, mode of action studies can be performed to determine if the molecule has a different mode of action than other pesticides. These collected data can then be disseminated to third parties, for example via the Internet.

Headings in this application are for convenience only and are in no way used to interpret any part of this application.

table part

Table 1. Compound numbers and structures

Table 2. Analysis data

a(°C)

b (thin layer; cm ^-1 )

Table 3: Rating table for green peach aphid and sweet potato whitefly

Table 4. Biological data of green peach aphid and sweet potato whitefly

Claims (65)

1. A composition comprising a molecule of formula 1: in (a) X is N or CR8; (b) R1 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, C(=X1)R9, C(= X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _nOR9 , or R9S(O) _nR9 , Wherein each of the substituted R1 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9); (c) R2 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, C(=X1)R9, C(= X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n OR9, or R9S(O) _n R9, Wherein each of the substituted R2 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9); (d) R3 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, C(=X1)R9, C(= X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n OR9, or R9S(O) _n R9, Wherein each of the substituted R3 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9); (e) R4 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, C(=X1)R9, C(= X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n OR9, or R9S(O) _n R9, Wherein each of the substituted R4 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9); (f) R5 is R11; (g) R6 is O, S, NR9, or NOR9; (h) R7 is substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, OR9S(O) _n R9, C(=X1)R9, C(=X1)OR9, R9C(=X1 )OR9, R9X2C(=X1)R9X2R9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)(R9S(O)nR9), _N (R9)C(=X1)R9 , SR9, S(O) _n OR9, R9S(O) _n R9, C ₁ -C ₆ alkyl OC(=O)C ₁ -C ₆ alkyl, OC ₁ -C ₆ alkyl C ₁ -C ₂₀ hetero Cyclic group, C ₁ -C ₆ alkyl C ₁ -C ₂₀ heterocyclyl, C ₁ -C ₆ alkyl S(=N-CN)(C ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl S(O)(=N-CN)(C ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl S(O) _n (C ₁ -C ₆ alkyl, C ₁ -C ₂₀ heterocyclyl), C ₁ -C ₆ alkyl S(O)(=N-CN)(C ₁ -C ₆ alkyl-C ₁ -C ₂₀ heterocyclyl), C ₁ -C ₆ alkyl NH(C(=O) OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl C(=O)OC ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl (C ₆ -C ₂₀ aryl) NH(C(= O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl (SC ₁ -C ₆ alkyl) NH (C(=O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl (SC ₁ -C ₆ alkyl-C ₆ -C ₂₀ aryl)NH(C(=O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl (NHC(=O)OC ₁ -C ₆ alkyl C ₆ -C ₂₀ aryl) NH(C(=O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl (OC ₁ -C ₆ alkyl C ₆ -C ₂₀ aryl) NH(C(=O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl N(C ₁ -C ₆ alkyl)(C(=O)OC ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl NH (C ₁ -C ₆ alkyl), C ₆ -C ₂₀ arylSC ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkyl-N (C ₁ -C ₆ alkyl) ( C(=O)C ₁ -C ₆ alkyl (C ₆ -C ₂₀ aryl), C ₁ -C ₆ alkyl N (C ₁ -C ₆ alkyl) (C ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl N (C ₁ -C ₆ alkyl)(S(O) _n C ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl N(C ₁ -C ₆ alkyl) (S(O) _n C ₁ -C ₆ alkene C ₆ -C ₂₀ aryl), C ₁ -C ₆ alkyl N(C ₁ -C ₆ alkyl) (C(=O)C ₁ -C ₂₀ heterocyclyl), C ₁ -C ₆ alkyl N(C ₁ -C ₆ alkyl)(C(=O)OC ₁ -C ₆ alkylC ₆ -C ₂₀ aryl), NH(C ₁ -C ₆ alkylS(O) _n C ₁ -C ₆ alkyl), NH (C ₁ -C ₆ alkyl S(O) _n C ₆ -C ₂₀ aryl), C ₁ -C ₆ alkyl (S(O) _n C ₁ -C ₆ alkyl) ( C(=O)C ₁ -C ₆ alkylS(O) _n (C ₁ -C ₆ alkyl), or R9S(O) _n (NZ)R9, Wherein each of the substituted R7 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9), C(=X1)R9, C(=X1)OR9, C(=X1)N(R9) ₂ , =X2, N(R9) ₂ , S(=X2) _n R9, R9S(O) _n R9, S(O) _n N(R9) ₂ ; (i) R8 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, OR9, C(=X1)R9, C(= X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n R9, S(O) _n OR9, or R9S (O) _n R9, Wherein each of the substituted R8 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ - C ₂₀ heterocyclyl (wherein each substitutable substituent may be optionally substituted with R9); (j) R9 (each independently) is H, CN, substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ ring Alkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, S(O) _n C ₁ -C ₆ alkyl, N(C ₁ - C ₆ alkyl) ₂ , Wherein each of the substituted R9 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OC ₁ -C ₆ alkyl, OC ₁ -C ₆ haloalkyl, S(O) _n C ₁ -C ₆ alkyl, S(O) _n OC ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, or C ₁ -C ₂₀ heterocyclic; (k) R10 is H, F, Cl, Br, I, CN, NO ₂ , substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₁ -C ₆ alkoxy, substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9) ₂ , N(R9) ₂ , N(R9)C(=X1)R9, SR9, S(O) _n OR9, or R9S(O) _n R9, Wherein each of the substituted R10 has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, S(O) _n OR9, or C ₆ -C ₂₀ aryl (wherein each Substitutable substituents may optionally be substituted with R9); (l) n is (each independently) 0, 1, or 2; (m) X1 is (each independently) O or S; (n) X2 is (each independently) O, S, =NR9, or =NOR9; (o) R11 is Q ₁ (C≡C)R12, wherein Q ₁ is a bond, substituted or unsubstituted C ₁ -C ₆ alkyl, substituted or unsubstituted C ₂ -C ₆ alkenyl, substituted or unsubstituted C ₂ -C ₆ alkynyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₂ -C ₁₀ cycloalkoxy, substituted or unsubstituted C ₁ -C ₆ alkyl OR9, substituted or unsubstituted C ₁ -C ₆ alkyl S(O) _n R9, substituted or unsubstituted C ₁ -C ₆ alkyl S(O) _n (=NR9) , substituted or unsubstituted C ₁ -C ₆ alkyl N(R9) (wherein (C≡C) is directly connected to N via a bond), substituted or unsubstituted C ₁ -C ₆ alkyl N(R9) _2. Substituted or unsubstituted C ₂ -C ₆ alkenyloxy, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl, substituted or unsubstituted C ₀ -C ₆ alkyl C(=R6 )C ₀ -C ₆ alkyl R9, substituted or unsubstituted C ₀ -C ₆ alkyl C(=R6)OR9, substituted or unsubstituted C ₁ -C ₆ alkylOC ₀ -C ₆ alkyl C(=R6)R9, substituted or unsubstituted C ₁ -C ₆ alkyl N(R9)(C(=R6)R9), substituted or unsubstituted C ₁ -C ₆ alkyl N(R9) (C(=R6)OR9), substituted or unsubstituted C ₀ -C ₆ alkyl C(=R6)C ₀ -C ₆ alkyl N(R9) (where (C≡C) is directly bonded to N through a bond Link), substituted or unsubstituted C ₀ -C ₆ alkyl C(=R6)C ₀ -C ₆ alkyl N(R9) ₂ , OR9, S(O) _n R9, N(R9)R9, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₁ -C ₂₀ heterocyclyl, Wherein each of the substituted Q ₁ has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO ₂ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ haloalkyloxy, C ₂ -C ₆ haloalkenyloxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₁₀ halocycloalkenyl, OR9, SR9, S(O) _n R9, S (O) _n OR9, C ₆ -C ₂₀ aryl, or C ₁ -C ₂₀ heterocyclyl, R9 aryl, C ₁ -C ₆ alkyl OR9, C ₁ -C ₆ alkyl S(O) _n R9 (wherein each substitutable substituent may optionally be substituted with R9) Optionally, _Q1 and R7 can be connected in a ring arrangement, wherein optionally, this arrangement can have one or more heterogeneous compounds selected from O, S, or N in the ring structure connecting _Q1 and R7. atom; (p) R12 is Q1 (except for the case where _Q1 is a bond), F, Cl, Br, I, Si(R9) ₃ (wherein each R9 is independently selected), or R9; and (q) Z is CN, NO ₂ , C ₁ -C ₆ alkyl (R9), C(=X1)N(R9) ₂ . 2. The composition of claim 1, wherein said X in said molecule is CR8. 3. The composition of claim 1, wherein said R1 is H in said molecule. 4. The composition of claim 1, wherein said R2 is H in said molecule. 5. The composition of claim 1, wherein said R3 is H in said molecule. 6. The composition of claim 1, wherein said R4 in said molecule is halogenated or unsubstituted _C1 - _C6 alkyl. 7. The composition of claim 1, wherein said R4 in said molecule is F, Cl, or unsubstituted _C1 - _C2 alkyl. 8. The composition of claim 1, wherein said R4 is Cl, or _CH3 in said molecule. 9. The composition of claim 1, wherein said R5 in said molecule is a substituted or unsubstituted _C1 - _C6 alkyl C≡CR12. 10. The composition of claim 1, wherein said R5 in said molecule is unsubstituted _C1 - _C6 alkyl C≡CR12. 11. The composition of claim 1, wherein said R5 in said molecule is _CH2C≡CH . 12. The composition of claim 1, wherein said R6 is O in said molecule. 13. The composition of claim 1, wherein said R7 in said molecule is a substituted or unsubstituted _C1 - _C6 alkyl, OR9, or R9S(O) _nR9 . 14. The composition of claim 1, wherein said R7 in said molecule is a substituted _C1 - _C6 alkyl, wherein said substituents are one or more halogens. 15. The composition of claim 1, wherein said R7 in said molecule is a substituted _C1 - _C6 alkyl group, wherein said substituents are one or more F or Cl or combinations thereof. 16. The composition of claim 1, wherein said R7 is a substituted _C1 - _C6 alkyl in said molecule, wherein said substituents are one or more F. 17. _The composition of claim 1, in said molecule said R7 is _CH2CF3 . 18. The composition of claim 1, wherein said R7 in said molecule is unsubstituted _C1 - _C6 alkyl. _19. The composition of claim ₁ , wherein said R7 in said molecule is CH( _{CH3 ) 2} , _CH3 , C( _CH3 ) ₃ , or _CH2CH2CH2CH3 . 20. The composition of claim 1, in said molecule said R7 is OR9. 21. The composition of claim 1, wherein said R7 is O(unsubstituted _C1 - _C6 alkyl) in said molecule. 22. The composition of claim 1, in said molecule said R7 is OC( _CH3 ) ₃ . 23. The composition of claim 1, wherein said R7 in said molecule is R9S(O) _nR9 . 24. The composition of claim 1, wherein said R7 in said molecule is (unsubstituted _C1 - _C6 alkyl)S(unsubstituted _C1 - _C6 alkyl). 25. The composition of claim 1, wherein _said R7 in said molecule is _CH2CH ( _CH3 ) _SCH3 , _{CH2CH2SCH3 ,} CH( _CH3 ) _{2SCH3 ,} or CH( _CH3 ) _{CH2SCH3 .} 26. The composition of claim 1, wherein said R8 is H or halogen in said molecule. 27. The composition of claim 1, wherein said R8 is H, F, or Cl in said molecule. 28. The composition of claim 1, wherein said R8 is H or F in said molecule. 29. The composition of claim 1, wherein in said molecule said R9 is unsubstituted _C1 - _C6 alkyl. 30. The composition of claim 1, wherein said R10 in said molecule is H or unsubstituted _C1 - _C6 alkyl. 31. The composition of claim 1, wherein said R10 is H or _CH3 in said molecule. 32. The composition of claim 1, wherein said n is zero in said molecule. 33. The composition of claim 1, wherein said molecule is 34. The composition of claim 1, further comprising: (a) one or more compounds having acaricidal, algicidal, avulicidal, bactericidal, fungicidal, herbicidal, insecticidal, molluscicidal, nematicidal, rodenticidal, or virucidal properties; or (b) one or more anti-feeding agents, bird repellents, chemical biocides, herbicide safeners, insect attractants, insect repellants, mammal repellants, mating disruptors, plant activators, plant growth modulator, or synergist compound; or (c)(a) and (b). 35. The composition of claim 1, further comprising one or more compounds selected from the group consisting of (3-ethoxypropyl)mercuric bromide, 1,2-dichloropropane, 1,3-dichloro Propylene, 1-methylcyclopropene, 1-naphthol, 2-(octylthio)ethanol, 2,3,5-tri-iodobenzoic acid, Caoyaping, Caoyaping-dimethylammonium, Caoyaping Ping-lithium, Caoyaping-potassium, Caoyaping-sodium, 2,4,5-T, 2,4,5-T-2-butoxypropyl, 2,4,5-T-2- Ethylhexyl, 2,4,5-T-3-butoxypropyl, 2,4,5-T-butyric acid, 2,4,5-T-butoxypropyl ester, 2,4,5- T-butoxyethyl ester, 2,4,5-T-butyl, 2,4,5-T-isobutyl, 2,4,5-T-isooctyl, 2,4,5-T- Isopropyl, 2,4,5-T-methyl, 2,4,5-T-pentyl, 2,4,5-T-sodium, 2,4,5-T-triethylammonium, 2, 4,5-D-Triethanolamine, 2,4-D, 2,4-D-2-Butoxypropyl, 2,4-D-2-Ethylhexyl, 2,4-D-3-Butyl Oxypropyl, 2,4-D-ammonium, 2,4-D-butyric acid, 2,4-D-butyric acid-butyl, 2,4-D-butyric acid-dimethylammonium, 2,4-D-butyric acid Acid-isooctyl, 2,4-D-butyrate-potassium, 2,4-D-butyrate-sodium, 2,4-D-butoxyethyl ester, 2,4-D-butyl, 2,4- D-diethylammonium, 2,4-D-dimethylammonium, 2,4-D-diolamine, 2,4-D-dodecyl ammonium, Saixin, Phosphate, 2,4-D -Ethyl, 2,4-D-heptyl ammonium, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D- Isopropylammonium, 2,4-D-lithium, 2,4-D-methylheptyl ester, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl Base, 2,4-D-potassium, 2,4-D-propyl, 2,4-D-sodium, 2,4-D-glycoside, 2,4-D-tetradecyl ammonium, 2 ,4-D-triethylammonium, 2,4-D-tri(2-hydroxypropyl)ammonium, 2,4-D-triethanolamine, 2iP, 2-methoxyethylmercuric chloride, 2-benzene Phenylphenol, 3,4-Diamine, 3,4-Dibutyric Acid, 3,4-Dipropionic Acid, 4-Aminopyridine, p-Chlorophenoxyacetic Acid, P-Chlorophenoxyacetic Acid-Potassium, p-Chlorophenoxyacetic Acid -Sodium, chlorphenoxybutyric acid, chlorphenoxypropionic acid, 4-hydroxyphenylethyl alcohol, 8-hydroxyquinoline sulfate, 8-phenylmercurioxyquinoline, avermectin, inducer, ACC, acephate, acaricide Quinone, Acetamiprid, Muscaphos, Acetochlor, Ethophos, Acetoprole, Activated Ester, Activated Ester-S-Methyl, Acifluorfen, Acifluorfen-Methyl, Acifluorfen Ether-sodium, aclofenac, acrep, bifenthrin, acrolein, acrylonitrile, acypetacs, acypetacs-copper, acypetacs-zinc, alachlor, acepincarb, prothiocarbendazim, aldicarb , allethrin, aldisulfonecarb, aldrin, allethrin, allicin, diacrylamide, azromycin, dioxazone, dioxazone-sodium, allyl alcohol, pest control Granville, pentachloropentanone acid, α-cypermethrin, α-endosulfan, oxazan, terzinone, ametryn, teroxazin, amifenone, seed dressing, saithion, amidoflumet , rimsulfuron-methyl, methoxur, cypromic acid, cypromic acid-methyl ester, cypromic acid-potassium, aminopyralic acid, aminopyralic acid-potassium, aminopyralic acid-tri( 2-Hydroxypropyl) ammonium, methamidofos, fenfofos, indoxasulfame, fenoxafos, carbamifos oxalate, amitraz, grass-killer, ammonium sulfamate, α-naphthalene Ammonium acetate, dysonium, 1-aminopropyl phosphate, neonicotinoid, cyprodinol, difenazol, sulphate, surauron, anthraquinone, Antu, cyclophosphine, acetap, Arsenic trioxide, arsenic thiram, aspirin, sultrapyr, sulphonyl-potassium, sulphonyl-sodium, ethidasone, atraton, atrazine, golden zymin, aviglycine, aviglycine hydrochloride, oxygen Cycloconazole, azadirachtin, fenpyridine, pyroxaphos-methyl, rimsulfuron tetrazole, cotton-phos-phos, acetophos, azide, thiram, azobenzene, triazotin, azophos , Azoxystrobin, bachmedesh, oat spirit, barium hexafluorosilicate, barium polysulfide, smoke pyrethrum, BCPC, flubutyramid, benalaxyl, benalaxyl-M, grass-killing, grass-killing- Dimethylammonium, bencarbazol-ethyl, bencarbazone-potassium, bencarbazone, benclothiaz, bentacarb, benfluralin, carbofuran, furazone, maprozil, benomyl, and chlorthiazide oxazine, fenoxafos, quinone oxime hydrazone, bensulfuron-methyl demethylate, bensulfuron-methyl, diazanphos, insecticide, bentaluron, bentazone, bentazone-sodium, benthiazil, benzene Thifluzamide-isopropyl, fenthiocyanate, benzacil, methazine, carbamide-ammonium, benzalkonium chloride, benzamacril, benzamacril-isobutyl ester, benzamorf, bimiflumezone, benzalkon Amines, benzobicyclones, metazadone, fomesulfazone, phenyl hydroxamic acid, benzamide, cylin, cylin-ethyl, benzothiuron, benzyl benzoate, benzyl adenine , berberine, berberine hydrochloride, β-cyfluthrin, β-cypermethrin, bethoxazin, bicyclopyzadone, bifenazate, methylcarbafen, bifenthrin, pyrflustrobin, dipropylamine Acyl phosphine, bialaphos-sodium, Lexa mite, cyanide, bio-allethrin, resmethrin, bio-permethrin, bio-resmethrin, biphenyl, bisazir, yecumazole , bispyribac, bispyribac-sodium, triflubenzuron, bifentriazole, thiochlorophene, bixafen, grievin, borax, Bordeaux mixture, boric acid, boscalid, brassinolide , ethyl brassinolide, bark beetle sex pheromone, brodifacoum, bromafenthrin, bromafluthrin, bibacil, bibacid-lithium, bibacid-sodium, bromadiolone, bromadiamide, Bromoresmethrin, bromofenfos, bromoacetamide, furoxynil, bromobutyramid, Bromofenac, bromo-DDT, bromophenoxim, bromthion, bromthion-ethyl, bromofen, bromoxynil, bromoxynil, butyryl bromoxynil, heptanoyl bromoxynil, octanoyl bromide Benzonitrile, Bromoxynil-Potassium, Bromoxynil, Fuconazole, Bronopol, Zenzat, Hexacarb, Buminafos, Ethyrimol Sulfonate, Buprofezin, Burgundy Mixture, Buxiao An, animal insects, butachlor, fluprofen, fenfos, pyrimthiofos, methoxam, permethrin, temazepor, buthiazine, buthiuron, butanonecarb, butyl Esterphosphine, repellent, butaclocarb, secbutaline, butazone, clodone, butylamine, butyrate, cacodylic acid, sulfuryl phosphorus, mefentrachlor, calcium arsenate, chlorine Calcium acid calcium, calcium cyanamide, lime sulfur mixture, didicalcium, gram sulfamate, toxaphene, camphor, captafol, captan, morphangicarb, chlordicarb, carbaryl, carba grass Carbendazim, carbendazim, carbendazim besylate, carbendazim sulfite, bisamide, carbofuran, carbon disulfide, carbon tetrachloride, trithion, carbosulfan, texazole Granitamide, ethylene oxide carbon dioxide mixture, wiltazol, mefentrazone, mefentrazone-ethyl, cyproamid, cartap, cartap hydrochloride, carvacrol, carvone, CDEA, Yekuyne, CEPC, ceralure, CHeshunt mixture, acarid, polyglucosamine, methenazole, methoxypyramid, chloralose, fenfen, fenfen-ammonium, fenfen-di Alcohol amine, chloramphenicol-methyl, chlorfenazol-methyl ammonium, chloramphenicol-sodium, chloramidophos, chloramphenicol, Chloraniformethan, tetrachloroquinone, butyramid, chlorantraniliprole, Propyloxypyr, Propyloxypyr-propargyl, Colazine, Fabfen, Dibenzuron, Bornemidan, Chlorbroron, Chloralkyne, Chlordane, Capron, Dimeform, Dimeform hydrochloride , Chlorethrin, Phosphate Oxychloride, Chloreturon, Falzak, Facyl-Ammonium, Falaxy-Sodium, Chlorfenapyr, Chlorbendazole, Fofol, Oat Ester, Fecapyl, Dietamite Special, poison insect fear, chlorfluazuron, fluoropyrimazole, Chlorfluren, Chlorfluren-methyl ester, plastic alcohol, plastic alcohol-methyl, chlorpyramid, chlorimuron-methyl deethylate, chlorimuron-methyl, chloromethylthio Phosphorus, chlormequat, chlormequat, ethyl chloride, cloquat, ethyl fofol, chlorinated naphthalene, chloroform, itomin, diflubenzuron, chloroanisole, chrysanthemum, chlordiquat sodium salt, Chloropicrin, Trichloropropionic Acid, Propyl Fofol, Chlorothalonil, Chloromeron, Subtilon, Hydroxydiclonil, Tributylchlorobenzylphosphine, Tributylchlorobenzylphosphine Chloride, Chlorophom, Chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos methyl, tetrachloroquinoxaline, chlorsulfuron, chlorophthalic acid, chlorophthalic acid-dimethyl, chlorophthalic acid-monomethyl, chlorosulfur Amidamide, chrysanthemum-phos, biclofenac, choline chloride, cyclotraniliprole, cinerin I, cinerin II, cinerin, indoxafop-methyl, cycloheptafen, etesulfuron, ciobutide, triclodone, L-anti-pyrethrin, clethodim, chlorpyridone, iodoclodin-propargyl, clodinafop-propargyl, clofencarb, clofencet, clofencet-potassium, tetramite oxazine, clofibrate, Chloropyrid, Chloropyrid-Isobutyl, Clomazone, Echinochlor, Toncarp, Cycloclotrione, Clopyralid, Clopyralid-Methyl Ester, Clopyralid-Alcohol Ammonium, clopyralid-potassium, clopyralid-tris(2-hydroxypropyl)ammonium, cloquintocet, cloquintocet-mexyl, cloransulam, clopyralid-sulam, iodosalam, clothianidin, cloransulam Azole, citric acid, citric acid-sodium, CMA, codlelure, thiazolphos, copper acetate, copper acetyl arsenite, copper arsenate, basic copper carbonate, copper hydroxide, copper naphthene carboxylate, oleic acid Copper, copper oxychloride, copper silicate, copper sulphate, copper zinc chromate, chlorwarfarin, carfafarin, musphos, coumoxystrobin, fenphos, coumoxystrobin, holpocarb, chloramphenicol , chlorpromazin, ether chloramine, cresol, mouse Lisi, crotamiton, baduphos, animal husbandry phosphorus, sodium fluoroaluminate, muscarinone, furunil, benturon, fungcarb, oxidation Cuprous, curcumol, cyanamide, cyanazazine, cyanazine, benzophosphine, cypronil, crotophos, cyanraniliprole, cyazofamid, cybutryne, cycloheximide, naphthenic anilide, cyclopyrethrin , Cyclobadil, Cycloheximide, Cyclofenate, Promethrin, Cyprosulfuron, Cyclochloridon, Cyclofluron, Cyenopyrafen, Cyflufenamide, Cyflufen, Cyfluthrin, Cyanofluoride Grass-methyl, cyhalofop-butyl, cyhalothrin, tricyclic tin, cymiazole, cymiazole hydrochloride, cymoxanil, acetamide, cyanendazim, cypermethrin, pasturate, chlorinated pastureate , phenetrin, ciprozine, tricyclic cyfechlor, cyproconazole, cyprodinil, oxyprostrobin, cyprosulfamide, cyprosulfamide, cyromazine, cyprophos, vanillon, thatch Acryl, dacet-calcium, daquat-magnesium, daquat-sodium, butyrhydrazide, pyridoxone, damanon, damanon-sodium, dibromochloropropane, d-camphor, dichloroisopropyl ether, production-increasing amine , DDT, Profencarb, Decaphostin, Mecarbofuran, Dehydroacetic Acid, Isobutachlor, Deltamethrin, Tetraphos, Tetraphos-O, Tetraphos-S, Demeton, Demeton-methyl, Demeton-O, Demeton-O-methyl, Demeton-S, Demeton-S-methyl, Demeton-sulfone, beetan, diquat, dextrotrans Propargyl permethrin, diafenthiuron, chloroimophos, avenate, dimethicone, diatomaceous earth, diazinon, dibutyl phthalate, dibutyl succinate, dicamba, Dicamba-diethylene glycol amine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-methyl, dicamba-alcoholamine, dicamba-potassium, dicamba- Sodium, dicamba-triethanolamine, isochlorphos, dichlorflunil, demiphos, benflusulfonamide, dichlornaphthaquinone, chlorquanrone, dichlorflurenol, dichlorflurenol-methyl ester, benzylamine, allyl Amamide, Dichlorophen, 2,4-Dipropionate, 2,4-Dipropionate-2-Ethylhexyl, 2,4-Dichlorpropionate-Butoxyethyl Ester, 2 , 4-Dipropionate-Dimethylammonium, 2,4-Dipropionate-Ethyl Ammonium, 2,4-Dipropionate-Isooctyl, 2,4-Dipropionate-Methyl, Purified 2,4- Trichlorpropionate, 2,4-propionate-2-ethylhexyl, 2,4-propionate-dimethylammonium, 2,4-propionate-potassium, 2,4-propionate- Sodium, dichlorvos, genozolin, chlortriazol, diclofenac, diclofen, diclofen-methyl, pyridazol, pyridazol-sodium, nicloramine, sulfasulfame, dicofol , dicoumarol, N-(3-methylphenyl) methyl carbamate, dicrotophos, cyclopronil, dicyclonon, dieldrin, acaricide, diethyl herbicide, diethyl dichloride herbicide bis, metolachlor, metolachlor-ethyl, dimethocarb, dietholate, diethylpyrocarbonate, DEET, mudec, difenoconazole, flufenac, flufenal Acrylic acid-ethyl, cumulon, phenotylate, pheasantil methosulfate, thiafafarin, diflovidazin, diflubenzuron, diflufenamide, diflupyrone, diflupyrone-sodium, fluoride Azoxystrobin, furofuric acid, furofuric acid-sodium, dihydroxyprophylline, dimatif, perfluthrin, mefluphos, oxazolone, perazolone, sclerotin, dimacarb, mixed Dimecarb, Dimethenachlor, Pentazazin, Dimethenamid, Dimethenamid, Thiacetin, Dimethenamol, Dimethoate, Dimethomorph, Permethrin, Mosquito Repellent, Repellent Mosquito-methyl, chlorpyramid, difiacarb, dimethoxan, dexamethasone, kyresastrobin, acetofen, dinex-diclexine, pyridoxazole, dinicoxazole, R-diniconazole, ammonium flu Dinopro, Dinopro, Dinocap, Dinocap-4, Dinocap-6, Dinopro, Dilet, Nipentyl Ester, Pronitrophenol, Pentonitrophenol, Dinopro, Dimophen B Diphenoxylate, diophen-ammonium, diophen-diolamine, diophen-sodium, diophen-triethanolamine, nitrocapryl, dinotefuran, diophen, diophen acetate, nitrobutyl ester , diphenoxyfen, vegetable and fruit phosphorus, dioxincarb, dioxafos, dimethazine, diphacin-sodium, dibenzamide, diphenyl sulfone, diphenylamine, dileline, isopropyl, dithiopyridine, Diquat, diquat dibromide, basine, 2,4-sodium disulfide, disulfiram, dithionate, 2,4-sodium disulfide, bacteriophos, dicyanoanthraquinone, thiophene Phosphate, Disulfide, Dithiopyr, Diuron, d-Limonene, Zytriphos, Dinitrocresol, Dinitrocresol-Ammonium, Dinitrocresol-Potassium, Dinitrocresol-Sodium, Dodexin, Dodexin Acetate, Dodexin Benzoate, Dodexin, Dodexin Hydrochloride, Dodexin-Sodium, Dodine, Phenoxypyridine , Dominicalure, Doramectin, Hydrazinone, Sodium Arsine, Phosphate, EBEP, EBP, Ecdysterone, Fenfofos, Glycyrrhizin, Glycyrrhizin-Ethyl, Amamectin, Methylamino Abamectin benzoate, spinoxacarb, d-threnthrin, endosulfan, indo-acid, indo-acid-diammonium, indo-acid-dipotassium, indo-acid-disodium, intoxication Phosphorus, endrin, enestroburin, fenthion, epocholeone, parenol, epoxiconazole, Aipu Ribectin, sulfentrazone, fenpyridine, styrofoam, ergocalciferol, dichlorhexanamide, esdépalléthrine, S-fenvalerate, valproate, ethylene silicon, ecloconazole, etaphos, Disensulfuron, ethaboxam, gram chloramine, ethenfluridine, ethametsulfuron-methyl demethylated acid, ethametsulfuron-methyl, acetamide, ethephon, sulfthiuron, ethylthiobencarb, sulfur grass Di, ethion, ethazrazone, ethiprole, pyrimethrimol, cotton-phos-phos, efurazone, repellent alcohol, methazine, chlorofluorfen, chlorofluorfen-ethyl, ethyl Oxyquinoline, Ethoxysulfuron, Indole, Ethyl Formate, Ethyl α-Naphthylacetate, DiDiDi, Ethylene, Ethylene Dibromide, Ethylene Dichloride, Ethylene Oxide, Acetoallin, 2,3 -Ethylmercury Dihydroxypropyl Mercaptan, Ethylmercury Acetate, Ethylmercury Bromide, Ethylmercury Chloride, Ethylmercury Phosphate, Nitrosol, Ethyroxyfen, Ethylmercuric, Ethylmercuric Esters, etoxazole, terbendazim, acetofos, eugenol, grass bisan, oxafefenone, fenfofos, midazolidone, sodium sulfonate, fenamiphos, miprotonil, chloropyrimidine Alcohol, acesulfacarb, anti-metazole, fenazaquin, fenfenazole, fenbutatin, clofenazole, fenbutazone-ethyl, pimaphos, clofencarb, ethylfencarb, penflufenchrysin Esters, mefuramide, fenhexamid, seed coating ester, fenitrothion, fenhefen, secbucarb, 2,4,5-nylpropionic acid, 2,4,5-nylpropionic acid-3- Butoxypropyl, 2,4,5-nylpropionate-butoxypropyl, 2,4,5-nylpropionate-butoxyethyl, 2,4,5-nylpropionate-butyl , 2,4,5-nylpropionate-isooctyl, 2,4,5-nylpropionate-methyl, 2,4,5-nylpropionate-potassium, fenthiocarb, fenoxacrim, rice blastamide, Fenoxaprop, Fenoxaprop-ethyl, Fenoxaprop-P-P-P, Foxaprop-P-P-P-ethyl, Isoxaprop-P-P, Dioxycarb, Seed Dressing, Cypermethrin, Methanol Permethrin, fenpropidin, fenpropimorph, fenpyrazamine, pyraclofen, fenridazon, fenridazon-potassium, fenridazon-propyl ester, fenflux, fonsofos, chlorphenoxyethanol, thiazoprop-ethyl, thiazopyr Ling-Ethyl, Fenthion, Fenthion-Ethyl, Triphenyltin, Triphenyltin Acetate, Triphenyltin Chloride, Triphenyltin Hydroxide, Tetrametram, Fluorine, Feuron , Feuron TCA, fenvalerate, ferbam, hydrazone, ferrous sulfate, fipronil, wheat straw fluorine, wheat straw fluoride isopropyl ester, wheat grass fluoride, wheat straw fluoride methyl ester, wheat straw fluorine isopropyl ester . Difluazifop-methyl ester, fluazifop-methyl-ethyl, fluazifop-methyl-butyl ester, fluazinam, parafenpyr-methyl, pyridoxuron, flubendiamide, thiazopyr, flucarbazone-methyl , flucarbazone-sodium, flubisulfuron-methyl, chlorpheniramine, fluorochlorodiphenylsulfuron, hexanuron, flucyvalerate, fludioxonil, fluoridemite, fluensulfone, flufenacet, flufenerim , diflufenpyr, flufenuron, Fluprofen, flupyridoxazone-ethyl, flupyridoxazone-ethyl ester, flufiprole, bifenthrin, flufenamid, flumethiram, flumetsulam, trifluoxazine, fluoxene Oxalic acid, oxalic acid-pentyl ester, fluorine propargyl, chlorpropargyl, flumorphine, fluuron, fluopyram, fluopyram, fluoride mite, glucosamine, fluoroacetamide, trifluoro Nitroglycerin, oxyflufen, oxyflufen-ethyl, fluoroimide, pyrenzazone, fluorfen, trifluben, triflubenazole, fluoxastrobin, flumifenazole , flupropacil, fluramid, tetrafluoropropionic acid, tetrafluoropropionic acid-sodium, flupyradifurone, flupyrsulfuron-methyl demethylation acid, fluridoximuron-methyl, fluridoximuron-methyl sodium, fluoroquinazole, Jiecao Amine, fluorenbutyl, fluorenbutyl-butyl, fluorenbutyl-methyl, fluroxydone, fluroxydone, fluroxypyr, fluroxyrpyr-butoxypropyl, chlorofluoro Pyroxyacetic acid-methylheptyl ester, flurimol, fluorosulfonamide, furazone, flusilazole, sulfamethanil, dazaflu, dazaflu-methyl, fluthiazamide, fluoroamide, Fenconazole, fluvalinate, fluflufen, fluroxyfen, folpet, fomesafen, fomesafen-sodium, tefenthion, foramsulfuron, forchlorfenuron, Formaldehyde, fencloprid, fencloprid hydrochloride, anthion, carbacarb, carbacarb hydrochloride, woodphosphine, woodphosphine-ammonium, triethylphosphonic acid, aluminum triethylphosphonate, butyric acid Fenthion, chlorpyrifos-methyl, thiazophos, fenthion, frontalin, wheat suingin, fluroxyzin, fluroxyfen, flunafenopyl, fuphenthiourea, multi-effect acetal, furaxyl, furazolin Esters, Fulabi, furocarb, dimofuramide, furconazole, fureconazole, furfuralthrin, furfural, oxaconazole, seed dressing amine, thiophanate furazone, furoxyfen, refined Beta-cyhalothrin, γ-hexahexyl, glyphosate, gibberellic acid, gibberellin, glyphosate, glufosinate-ammonium, glufosinate-ammonium, refined glufosinate-ammonium, refined glufosinate-ammonium, Glufosinate-ammonium-sodium, pectin, glyoxime, glyphosate, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-isopropylammonium, glyphosate-monoammonium, Glyphosate-Potassium, Glyphosate-Sesquisodium, Glyphosate-Trimethylsulfur Salt, Glyphosate, Sinyl Ester, Trapezem Mixture, Griseofulvin, Biguanoctylamine, Biguanoctylacetic Acid Salt, quinolinyl acrylate, benzafen, terbufenhydrazide, sulfonamide, chlorpyrazosulfuron-methyl demethylate, chlorpyrazosulfuron-methyl, halopyr, fluroxyfop, flurpiridine Hexapyl, haloxyfop-pyl, haloxyfop-pyl-ethyl, haloxyfop-pyl-ethyl, haloxyfop-pyl-ethyl, haloxyfop-pyl-sodium, hexahexapyl, hexamethylmelamine, hexamethylphosphamide, dieldrin agent, heptachlor, heptafenphos, production-increasing oxime, thion, hexachloroacetone, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexaflumuron, hexafluoroarsinate, red Lurene, hexamide, hexazinone, hexylthiofos, hexythiazox, aldrin, holosulf, cyclobasin, sulfofosinate, cycloconazole, hydrazone, naphthalene sulfonate, slaked lime, hydrogen cyanide, methotrex Ethyl ester, hymexazol, quinocarb, indole acetic acid, indole butyric acid, icaridin, imazalil, imazalil Azolazole Nitrate, Imazalil Sulfate, Imazethapyr, Imazethapyr-Methyl, Imazethapyr, Imazethapyr-Ammonium, Imazapyr, Imazazole-Ammonium, Imazethapyr , imazethapyr - isopropyl ammonium, imazethapyr, imazethapyr - ammonium, imidazaquin - methyl, imidazaquin - sodium, imazethapyr, imazethapyr - ammonium, imazethapyr-methyl, sub Amazoles, neonicotinoids, imidacloprid, chlorothiaprid, biguanidine octylamine, biguanidine octylamine triacetate, biguanidine octylamine trialkylbenzenesulfonate, imidamethrin, anti-tandamide, indazolone, indaziflam , indoxacarb, bendaofenjing, iofensulfon, iodocarb, methyl iodide, iodosulfuron-methyl demethylate, iodosulfuron-methyl, iodosulfuron-sodium, iofensulfuron, iofensulfuron-sodium, iodosulfonil, Caprylyl-iodoxynil, iodoxenil-lithium, iodoxenil-sodium, oxazin, bacconazole, halobenazole, isofamidine, iprodione, valericincarb, propyridine, dentate beetle II Enol, Dendrobesteryl alcohol, Fenprofos, Isamidofos, Chlorazofos, Carclorazine, Bumidamide, Isocarbophos, Isocaramil, Isofaldrin, Isofenfos, Isofenfos-A Base, Isocarb, Metrametrione, Isocarbamone, Nitrogen Grass, Isoprocarb, Isoprofen, Inoprofen, Isoproturon, Methazone, Isopyrimol, Isoben-phos, Isotianil, Isoxuron, Isofenone, Isoxamide , clomazone, isoxadifen, isoxadifen-ethyl ester, clomazone, clomazone, oxazophos, abamectin, soaking phosphorus, japonilure, pyrapethrin, jasmothrin I, Jasmolin II, jasmonic acid, sulfazone, methylsyrbutan, melystrobin, oxalane, oxalen, iodophos, juvenile hormone I, juvenile hormone II, juvenile hormone III. Thienthrin, teramine, karetazan, karetazan-potassium, kasugamycin, kasugamycin hydrochloride, gramaphos, kelefan, ketospiradox, ketospiradox-potassium, sugar aminopurine, methoprene , phenoxystrobin, quinafe, lactofen, lambda-cyhalothrin, latilure, lead arsenate, cyclopyridine, lepimectin, bromophenylphosphine, lindane, lineatin, Liguron, acetamiphos , litlure, looplure, lufenuron, chlorpyracillin, glufosinate, thiazolphos, methyl arsinic acid, malathion, maleic acid hydrazide, benzyl malononitrile, dextrin-maltose complex agent, Arsine monoammonium, mancocopper, mancozeb, mandiprodil, maneb, matrine, phosphorus azide, 2-methyl-4-chloro, 2-methyl-4-chloro-2-ethylhexyl, 2 Methyl 4-chloro-butoxyethyl ester, 2-methyl-4-chloro-butyl, 2-methyl-4-chloro-dimethylammonium, 2-methyl-4-chloro-diolamine, 2-methyl-4-chloro-ethyl, 2-methyl-4-chloro-iso Butyl, 2-methyl-4-chloro-isooctyl, 2-methyl-4-chloro-isopropyl, 2-methyl-4-chloro-methyl, 2-methyl-4-chloro-alcoholamine, 2-methyl-4-chloro-potassium, 2-methyl-4-chloro-sodium , 2-methyl-4-chloroethyl thioester, 2-methyl-4-chloro-triethanolamine, 2-methyl-4-chlorobutyric acid, 2-methyl-4-chloro-butyric acid-ethyl, 2-methyl-4-chloro-butyric acid-methyl, 2-methyl-4-chloro-butyric acid -Sodium, o-amide, aphidphos, benzocarb, tetramethylphosphonate, 2-methyl-4-chloropropionic acid, 2-methyl-4-chloro-propionic acid-2-ethylhexyl, 2-methyl-4-chloro-propionic acid-dimethylammonium, 2 Mecoprop-diolamine, mecoprop-ethadyl, Mecoprop-isooctyl, Mecoprop-methyl, Mecoprop, Mecoprop, Mecoprop -2-Ethylhexyl, refined 2-methyl-4-chloropropionic acid-dimethylammonium, refined 2-methyl-4-chloro-propionic acid-isobutyl, 2-methyl-4-chloro-propionic acid-potassium, refined 2-methyl-4-chloropropionic acid-potassium, 2-methyl-4-chloropropionic acid-sodium, 2-methyl-4-chloropropionic acid-triethanolamine, methamidine, nitrophenol, nitrophenol acetate, decoy ester, mefenpyr-diethyl, mefenpyr, mefenpyr-diethyl, fluorine Sulfenamide, sulfentrazone-diolamine, sulfentrazone-potassium, megatomoic acid, aphithion, azoxyprodil, meperfluthrin, mephenate, diamidophos, mepiperium, mepezine , mepiquat pentaborate, rustamine, dinitrocrotonate, mercuric chloride, mercuric oxide, calomel, Defoliate phosphite, methatrazine, metsulfuron-methyl demethylate, metsulfuron-methyl, mesotrione, methotrexate, methyl sulfoxide, methflumizone, metalaxyl, refined metalaxyl, tetramer Acetaldehyde, Mebamura, Mebamura-ammonium, Mefenoxam, Memetrazone, Mebamura-Potassium, Mebamura-Sodium, Metrametram, Diether-chlorpyrazosulfuron-methyl, m- Chloroxypyrone, metconazole, mitipa, fluridazol, methylbenzhiuron, chrysanthemum, flufenpyrrole, methamidophos, sulfacarb, imazafen, furazone, thiaclofen Phosphorus, methiobencarb, methiocarb, thiosulfuron-methyl, methiocarb, oxaclofen, methazon, butenamidophos, orthopyrone, methomyl, methoprene, garazine , quinoline carboxylate, methothrin, methoxychlor, methoxyfenozide, benzotrione, methyl sterile, methyl bromide, methyl eugenol, methyl iodide, methyl isothiocyanate , methyl ethyl ester phosphine, methyl chloroform, methyl sulfauron, dichloromethane, methylmercury benzoate, cyanidinium methylmercury, methylpentachlorophenolmercuric, methyl neodecylamide, disenlian, pyran Bromoglurone, Metofluthrin, Metolachlor, Meprocarb, Phenoxystrobin, Sulfenpyramid, Methoxazone, Methoxuron, Metrafenone, Metrachlorone, Thioxetine Bacteramine, metsulfuron-methyl demethylate, metsulfuron-methyl, memethafos, zikewei, mirantan, milmectin, milbexime, disencycline, propamidofos, mirex, MNAF, mushroom Alcohol, molinate, molosultap, heptanamide, texazolone, monochloroacetic acid, monocrotophos, chlorguron, monosulfuron, monosulfuron-methyl, imauron, imauron TCA, cutting Grass fast, dichloride dichloride, morpholine guanidine, morpholine guanidine hydrochloride, thiofos, morzid, moxidectin, arsenazo monosodium, lutrene, myclobutanil, methionazol, N-( Ethylmercury)-p-toluenesulfoniline, Sodium Disen, Naphthalene Peptide Phosphate, Dibromophosphine, Naphthalene, Naphthalene Acetamide, Naphthalene Dicarboxylic Anhydride, Naphthalene Oxyacetic Acid, Napromine, Napropamide, Naphthalem, Naphthalene Ammonium-sodium, natamycin, oxabulong, spiroxamine, spiroxamine-olamine, nicosulfuron, nicotine, fenex, diclochlor, nitenpyram, nitrothiazide, Mesultraline, Trichloromethylpyridine, Penfencarb, Biben, Amofluorfen, Thiocyanate, Phthalstrobin, Ratyl, Fluoxetine, Protonicotine, Methron, Fluoride Urea, polyfluorourea, pyrimidine alcohol, OCH, octachlorodipropyl ether, octhilone, furamide, omethoate, turfone, orfralure, o-dichlorobenzene, rimsulfuron, oryctalure, oxime ether Bacteramine, amisulfame, osthole, ostramone, oxadiazil, propargyl oxadiazone, oxadiazone, oxadaxyl, oxamate, oxamyl, oxaquamin, oxadiazine -dimolamine, oxalazine-sodium, epoxysulfuron-methyl, chloroxazone, copper quinolate, quintraxalone, oximidazole, oximidazole fumarate, oxidized carboxyl, phosphoxide, isosuboxide Sulfone phosphorus, sulfone mixed with phosphorus, ethofurafen, fireworks matrine, oxytetracycline, oxytetracycline hydrochloride, paclobutrazol, piperacrid, p-dichlorobenzene, p-furone, paraquat, paraquat II Chloride, Paraquat Methosulfate, Parathion, Methyl Parathion, Chlorpheniridine, Grazate, Blasticate, Nonanoic Acid, Penconazole, Pencilone, Pendimethalin, Pentobenzene Penzafen, Flufenuron, Penoxsulam, Pentachlorophenol, Mechlorfen, Penthiopyrad, Pencypermethrin, Penoxazone, Fluoxenamide, Permethrin, Oxen Grass Ammonium, Cyclostrobin, Yekujing, Cotamamine, Fenthion, Betainin, Betainin-Ethyl, Acyluron, Phenothrin, Benfenfen, Daofengsan, Phenylmercuron , phenylmercuric acetate, phenylmercuric chloride, phenylmercury derivatives of catechol, phenylmercuric nitrate, phenylmercuric salicylate, phorate, tetramine, chlorthion, chlorine plague Phosphorus, thionate, thionate-methyl, glyphosate, imophos, parathion, phosphamide, phosphine, etprofocarb, phosphorus, triphosphostin, phoxim, Phoxim-Methyl, Tetrachlorophthalide, Amiloride, Amiloride-2-Ethylhexyl, Amiloride-2-Ethylhexyl, Amiloride-Methyl, Amiloride- Alcohol amine, amiloride-potassium, amiloride-triethylammonium, amiloride-tris(2-hydroxypropyl)ammonium, flupyramid, picoxstrobin, mouse end, mouse end -Sodium, pinoxaden, peripridine, piperonyl butoxide, synergone, diphenafos, pipequam, chrysanthemum, synergaldehyde, methamidophos, pirimicarb, pyrimidinox, Pirimiphos, Pirimiphos-methyl, Triclosinate, Zinc, Polyoxin, Paulomycin, Paulomycin-Zinc, Polythiane, Potassium Arsenite, Potassium Azide, Potassium cyanate, potassium gibberellic acid, potassium naphthenate, potassium polysulfide, potassium thiocyanate, potassium α-naphthalene acetate, pp'-DDT, dextroproparthrin, precocious factor I, precocious factor II, precocious factor Prochlorine III, pretilachlor, pyrimidine, flurimsulfuron-methyl demethylate, flurimsulfuron-methyl, allylbenzothiazole, prochloraz, prochloraz-manganese, methazol, cyclocyanazine, Pythium Li, amfluralin, profenofos, flufentrazone, ciproflurone, profluthrin, cyclazone, gambozine, gambozine-ethyl, prohexadione, prohexadione-calcium, prohydrojasmon . Chestphos, oxalic acid, fast-mite, mefurynethrin, propazine, amphetamine, aniline, propiconazole, propafen, propachlor, propoxur, propoxysulfuron-methyl, propylenesulfonate Long-sodium, synergistic ester, imidazole rimsulfuron, benzamide, propoxyquinoline, psoralactone, pinoxaden sulfenimine, benprodan, flusulfuron, ethiazophos , Thiofencarb, Thiofencarb Hydrochloride, Prothioconazole, Prothion, Phathion, Protrifenbute, Protrifenbute, Promethionate-Sodium, Propyramide, Bidanone, Pymetrozine, Pyran Ling, pyramethon, pyracloxamil, pyraclostrobin, pyraclofen, pyraclofen-ethyl, pyrimidinecarb, pyrimidinecarb, pyraclostrobin, pyraclostrobin, pyrasulfotole, pyrazolate, pyraprofos, pyrazosulfuron methyl deethylate, pyrazosulfuron methyl, pyrithion, benzamconazole, antipyrethrin, pyrethrin I, pyrethrin II, pyrethrin, pyribambenz-isopropyl ester, pyribambenz- Propyl ester, pyribencarb, saflufenacil, barnyard, chlorpyr, pyridaben, pyridafol, acetamiprop, pyridazinate, pyridate, pyrifluquinazon, pyrifluquinazone, pyrifluquinazon, pyriflufen, pyrimethanil, pyrimidin, pyrizachlor, pyrifluquina-methyl, pyrimisulfan, pyrimiphos, rodent excellent, trimethoprim, pyridyl alcohol, pyridyl alcohol, pyriproxyfen, pyrimisulfan, pyrimisulfone-sodium, pyrazacarb, pyroxaquinone, pyroxasulfone, pyrimisulfone Amines, chlormethopyridine, chlorpyramid, bitterwood, quinone, quinone sulfate, quinathion, quinathion-methyl, quinone hydrazone, quinclorac, clobenazole, chloroquine Acid, algae quinone, chlorophyll amine, quiseon, quinoxyfin, quinthion, pentachloronitrobenzene, quizalofop, quizalofop-ethyl, quizalofop-ethyl, quizalofop-ethyl base, quizalofuryl, fly repellent, mosquito repellent, pyrimazole, iodoxanamide, rebemide, resmethrin, thiocyanate, sativatin-III, ribavirin, sulfone pyrimide Sulfuron-methyl, rotenone, chrysanthemum, saflufenacil, saijunmao, sasenone, salicylanilide, sanguinarine, anisein, octamethylfos, red squid, another dingjin, micaotong, Ciprofen, selamectin, monoformamidine, monoformamidine chloride, synergistic chrysanthemum, sesamoline, ethoxydim, bimethafos, cyclofluron, siglure, insecticide silicon ether, poison Rat silicon, silica gel, silthiazil, simazine, silfluazole, simatone, sizazone, androcid, SMA, metolachlor, sodium arsenite, sodium azide, chlorine sodium fluoride, sodium fluoride, sodium fluoroacetate, sodium hexafluorosilicate, sodium naphthenate, sodium o-phenylphenate, sodium pentachlorophenate, sodium polysulfide, sodium thiocyanate, sodium α-naphthalene acetate, threonate Phosphorus, Spinosad, Acetate, Spirodiclofen, Spiromethidate, Spirotetramat, Spirooxamine, Streptomycin, Streptomycin Sesquisulfate, Strychnine, Mushrooms Metyrazol, Sulfateturon, Sulfateturon-Sodium, Sulcotrione, Cacaba, Sulfentram, Sufelam, Sulfluramid, Metsulfuron-methyl-demethylate, Metsulfuron-methyl , Sulfosulfuron, Ceretate, sulfoxaflor, sulfoxide, thioxime ether, sulfur, sulfuric acid, sulfuryl fluoride, azepine ester, thioprofos, pentylsulfone, methazone, τ-fluvalinate Ester, barnyard, thiafencarb, trichloroacetic acid, trichloroacetic acid-ammonium, trichloroacetic acid-calcium, TCA-ethadyl, trichloroacetic acid-magnesium, trichloroacetic acid-sodium, Didi, tebuconazole, Tebufenozide, tebufenpyr, ibuthoxyquin, pirimprofos, phosphatamine, Tethhiuron, Teclophthalein, Tetrachloronitrobenzene, thiram, Flufenuron, Tefluthrin, tefuryltrione, tembotrione , temefos, tepa, Tep, pyroxydone, cyclopentallethrin, terbutydine, terbutaline, terbutachlor, terbutysulfuric acid, methoxazone, terbutyzine, Tetracycline, tetracyclazole, tetrachloroethane, insecticide fear, tetrafluconazole, dicofen sulfone, fluoxon, tetramethrin, tetramethylfluthrin, hydroxylated tetramethylamine, acaricide, Mite good, thallium sulfate, dimethenamid, θ-cypermethrin, thiabendazole, thiacloprid, fluthianimil, thiamethoxam, thiapropionil, cyzolon, thiazole nicotinic acid, thiaclofos, thiabendonil, thiadiazolamide, thiencarbazone, thiencarbazone-methyl ester, thiensulfuron methyl acid, thifensulfuron, thifur Amide, mobisulfan, anti-chorcarb, thichlorobenimine, dime-sultap, dime-sultap hydrochloride, dime-sultap oxalate, copper thiadiazole, thiodicarb, monoclocarb, thiofluoroxime Ether, thiohempa, thimerosal, dithionate-methyl, nematophos, thiophanate, thiophanate-methyl, gram miticide, rodent, thiosultap, thiosultap-diammonium, dimehypo, monosultap, Thiotepa, thiram, difibrate, thiazilamide, Tuoan, Zhongcaodan, pyrizachlor, tioxymid, cyclolinecarb, tolclofos-methyl, tolfenpyr, toluene flusulfonamide, mercuric tolyl acetate , topramezone, trimethylbenzotrione, deltacypermethrin, perfenthrin, tralopyril, transfluthrin, transpermethrin, tratamide, triacontanol, triadimefon, triaconol, triafamone, meecam , Furbenfos, Imbudazole, Benfenthiat, Azoxystrobin, Tribesulfuron-methyl, Trimebicarb, Butyltriazole, Triazinflufen, Triazophos, Imazosin, Tribesulfuron-methyl Acid, Trisulfuron-methyl, Defoliant Phosphate, Tributyltin Oxide, Cyclopyr, Salicylamine, Trichlorfon, Isapiaphos-3, Phosphate, Triclopyr, Triclopyr-Butoxy Triclopyr-Ethyl Ethyl, Triclopyr-Ethyl, Triclopyr-Triethylammonium, Tricyclazole, Paraffin Oil, Promethacycline, Cadazine, Spiromorph, Chlorphenprofen, Trifloxystrobin, Triclopyr Flusulfuron-methyl, trifloxysulfuron-sodium, flufenazole, triflumuron, trifluralin, flusulfuron-methyl demethylation acid, flusulfuron-methyl, trifluroxyphenoxypropionic acid, trifluroxyphenoxy Propionic acid-methyl, trifluroxime, azinamine, trihydroxytriazine, carboxylate, trimethuron, trimethyluron, trimethoprim, trinexapac-ethyl, methoprene, indenazone, tripterygium Acetonin, turdac, fenfenazole, triflumesulfuron-methyl, trunc-call, uniconazole, uniconazole, formazol, uretipa, fenvalerate, validamycin, valifenalate, Warfarin, aphidion, imazamil, flupyrazole, mebaben, vinclozolin, warfarin, warfarin-potassium, warfarin-sodium, nitropyrphos, octostatin , Methastrobin, Methoxur, Xylenechlor, Xylenol, Methacarb, Inhibitorin, Cyanoxanil, Zeatin, Synergamine, ζ-Cypermethrin, Zinc Naphthenate, Zinc Phosphide , Zinc thiazole, Zinc zinc, Zirmet, zolaprofos, benzamid, sulfasulfuron-methyl, α-chloroethanol, α-ecdysone, α-multistriatin, and α-naphthaleneacetic acid. 36. The composition of claim 1, further comprising an agriculturally acceptable carrier. 37. The composition of claim 1, wherein said molecule is in the form of a pesticidally acceptable acid addition salt. 38. The composition of claim 1, wherein said molecule is in the form of a salt derivative. 39. The composition of claim 1, wherein said molecule is in the form of a hydrate. 40. The composition of claim 1, wherein said molecule is in the form of an ester derivative. 41. The composition of claim 1, wherein said molecule is in the form of a crystalline polymorph. 42. The composition of claim 1, wherein said molecule ^has2H in place ^of1H . 43. The composition of claim 1, wherein said molecule ^has14C in place ^of12C . 44. The composition of claim 1, further comprising a biopesticide. 45. The composition of claim 1, further comprising one or more of the following compounds: (a) 3-(4-Chloro-2,6-dimethylphenyl)-4-hydroxy-8-oxa-1-azaspiro[4,5]dec-3-en-2-one; (b) 3-(4'-chloro-2,4-dimethyl[1,1'-biphenyl]-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4, 5] Dec-3-en-2-one; (c) 4-[[(6-chloro-3-pyridyl)methyl]methylamino]-2(5H)-furanone; (d) 4-[[(6-chloro-3-pyridyl)methyl]cyclopropylamino]-2(5H)-furanone; (e) 3-Chloro-N2-[(1S)-1-methyl-2-(methylsulfonyl)ethyl]-N1-[2-methyl-4-[1,2,2,2- Tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide; (f) 2-cyano-N-ethyl-4-fluoro-3-methoxy-benzenesulfonamide; (g) 2-cyano-N-ethyl-3-methoxy-benzenesulfonamide; (h) 2-cyano-3-difluoromethoxy-N-ethyl-4-fluoro-benzenesulfonamide; (i) 2-cyano-3-fluoromethoxy-N-ethyl-benzenesulfonamide; (j) 2-cyano-6-fluoro-3-methoxy-N,N-dimethyl-benzenesulfonamide; (k) 2-cyano-N-ethyl-6-fluoro-3-methoxy-N-methyl-benzenesulfonamide; (l) 2-cyano-3-difluoromethoxy-N,N-dimethylbenzenesulfonamide; (m) 3-(difluoromethyl)-N-[2-(3,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazole-4-carboxamide; (n) N-ethyl-2,2-dimethylpropionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone; (o) N-ethyl-2,2-dichloro-1-methylcyclopropane-carboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone nicotine; (p)O-{(E-)-[2-(4-Chloro-phenyl)-2-cyano-1-(2-trifluoromethylphenyl)-vinyl]}S-methylthio Carbonate; (q) (E)-N1-[(2-Chloro-1,3-thiazol-5-ylmethyl)]-N2-cyano-N1-methylacetamidine; (r) 1-(6-chloropyridin-3-ylmethyl)-7-methyl-8-nitro-1,2,3,5,6,7-hexahydro-imidazo[1,2- a] pyridin-5-ol; (s) 4-[4-Chlorophenyl-(2-butylene-hydrazono)methyl)]phenyl methanesulfonate; and (t) N-Ethyl-2,2-dichloro-1-methylcyclopropanecarboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone. 46. The composition of claim 1, further comprising a compound having one or more of the following modes of action: acetylcholinesterase inhibitors; sodium channel modulators; chitin biosynthesis inhibitors; GABA and glutamate gates Chloride Channel Antagonist; GABA- and Glutamate-Gated Chloride Channel Agonist; Acetylcholine Receptor Agonist; Acetylcholine Receptor Antagonist; MET I Inhibitor; Mg-Stimulated ATPase Inhibitor; Nicotinic Acetylcholine Receptor ; midgut membrane disruptor; oxidative phosphorylation disruptor and ryanodine receptor (RyR). 47. The composition of claim 1, further comprising seeds. 48. The composition of claim 1, further comprising seeds that have been genetically modified to express one or more specialized traits. 49. The composition of claim 1, wherein said composition is encapsulated in a capsule, or placed on the surface of a capsule. 50. The composition of claim 1, wherein said composition is encapsulated in a capsule, or placed on the surface of a capsule, wherein said capsule has a diameter of about 100-900 nanometers or about 10-900 micrometers. 51. A method comprising applying the composition of claim 1 to a locus in an amount sufficient to control such pests to control such pests. 52. The method of claim 51, wherein said pest is selected from the group consisting of beetles, earwigs, cockroaches, flies, aphids, scales, whiteflies, leafhoppers, ants, wasps, termites, moths, butterflies, lice, grasshoppers, locusts, crickets , fleas, thrips, silverfish, mites, ticks, nematodes and Synthetica. 53. The method of claim 51, wherein the pest is from the phylum Nematodes or Arthropoda. 54. The method of claim 51, wherein the pest is from the subphylum Chelicoptera, class Myriapoda, or class Hexapoda. 55. The method of claim 51, wherein the pest is from the class Arachnida, Syndrome, or Insecta. 56. The method of claim 51 , wherein said pest is from the order Liceoptera, Coleoptera, Dermatoptera, Blatella, Diptera, Hemiptera, Hymenoptera, Isoptera, Lepidoptera, Trichophaera , Orthoptera, Flea, Thysanoptera, Thysanoptera, Acarina, or Synthetica. 57. The method of claim 51, wherein the pest is green peach aphid or sweet potato whitefly. 58. The method of claim 51, wherein the amount is from about 0.01 grams/ha to about 5000 grams/ha. 59. The method of claim 51, wherein the amount is from about 0.1 g/ha to about 500 g/ha. 60. The method of claim 51, wherein the amount is from about 1 gram/ha to about 50 grams/ha. 61. The method of claim 51, wherein said locus is apple, corn, cotton, soybean, canola, wheat, rice, sorghum, barley, oats, potato, orange, alfalfa, lettuce, strawberry, tomato, pepper, crucifer Areas where plants of the genus family, pears, tobacco, almonds, sugar beets, or beans are growing or their seeds are about to be sown. 62. The method of claim 51, further comprising applying the composition to a genetically modified plant that has been genetically modified to express one or more specialized traits. 63. The method of claim 51, wherein said composition further comprises ammonium sulfate. 64. A method comprising: administering orally or topically the composition of claim 1 to a non-human animal to control endoparasites, ectoparasites, or both endoparasites and ectoparasites. 65. A method comprising applying the composition of claim 1 to a plant at a time of low pest activity to enhance the health, yield, vigor, quality, or tolerance of said plant.